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(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Struktur
376608-71-8
CAS-Nr.
376608-71-8
Englisch Name:
(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
Synonyma:
(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine;(1R,2S)-2-(3,4-difluorophenyl)cyclopropanaMine (R)-2-hydroxy-2-phenylacetate;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)ethanoate;(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine (R)-2-hydroxy-2-phenylacetate;(1R,2R)-2-(3,4-difluorophenyl)cyclopropanamine(S)-(carboxylato(phenyl)methyl)holmium;(1R 2S)-2-(3 4- DIFLUOROPHENYL) CYCLOP ROPANAMINIUM (2R)- HYDROXY(PHENYL) ETHAN OATE MANDELIC ACID SALT;EX-7182;2S)-2-(3;Ticagrelor int4;)ethanoate, 98%
CBNumber:
CB62535571
Summenformel:
C17H17F2NO3
Molgewicht:
321.32
MOL-Datei:
376608-71-8.mol
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(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Eigenschaften

Schmelzpunkt:
161 °C
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
Farbe
White to Off-White
Major Application
Pharmaceutical intermediates
InChI
InChI=1/C9H9F2N.C8H8O3/c10-7-2-1-5(3-8(7)11)6-4-9(6)12;9-7(8(10)11)6-4-2-1-3-5-6/h1-3,6,9H,4,12H2;1-5,7,9H,(H,10,11)/t6-,9+;7-/s3
InChIKey
GUESUQPLVFMJIT-RUKVIUEPNA-N
SMILES
[C@H](C1C=CC=CC=1)(O)C(=O)O.N[C@@H]1C[C@H]1C1C=CC(F)=C(F)C=1 |&1:0,12,14,r|
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
S-Sätze: 24/25
HS Code  29181990
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

(1R, 2R)-2-(3, 4-difluorophenyl) cyclopropanamine(S)-(carboxylato(phenyl)methyl) holmium is a useful pharmacological intermediate. It is utilized as an intermediate of trcagrelor, which is a platelet aggregation inhibitor used for prevention of thrombotic events occurring in people with acute coronary syndrome or myocardial infarction.

Chemische Eigenschaften

White to off-white powder

Verwenden

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine is an intermediate in the preparation of orally active reversible P2Y12 receptor antagonists for the prevention of thrombosis.

Synthese

1. Trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitro cyclopropane (215.0 g) was added to the pre-cooled methanolic hydrochloric acid (6.0% to 7% w/w HCl, 4300 ml), followed by cooling the mass to -5 to 0° C. Zinc dust (343.71 g) was added to the resulting mass over a period of 2 to 3 hours while maintaining the temperature at -5 to 0° C. The reaction mass was stirred further for 2 hours at -5 to 0° C. After completion of the reaction, the reaction mass was filtered through a hyflo bed and the bed was washed with methanol (2×215 ml). The main filtrate and washings were combined, followed by distillation under reduced pressure.
2. The resulting residue was dissolved in dichloromethane (1075 ml) and then cooled to 10 to 15° C. 25% Aqueous ammonia solution (1290 ml) was added to the cooled solution while maintaining the temperature at below 30° C. The resulting reaction mass was stirred for 15 minutes, followed the by layer separation. The resulting aqueous layer was extracted with dichloromethane (2×537.5 ml) and then combined with the main dichloromethane layer. The combined dichloromethane layer containing the product was extracted thrice with aqueous hydrochloric acid (645 ml of conc. hydrochloric acid mixed with 1935 ml water, 3×865 ml). The aqueous acidic layer containing the product was combined and washed with dichloromethane (645 ml). Dichloromethane (1075 ml) was added to the acidic aqueous layer, followed by the addition of 25% aqueous ammonia solution (1505 ml) while maintaining the temperature at below 30° C. The resulting reaction mass was extracted with dichloromethane (2×645 ml) and then combined with the main dichloromethane layer. The combined dichloromethane layer containing the product was washed with water (645 ml) and evaporated to dryness under reduced pressure.
3. The resulting residue was dissolved in methanol (430 ml), followed slow addition of (R)-(-)-mandelic acid solution (107.5 g in 645 ml methanol) over a period of 40 to 60 minutes while maintaining temperature at 20 to 25° C. The resulting slurry was stirred further for 12 hours at 20 to 25° C., followed by further cooling to 0 to 5° C. The cooled solution was stirred for 2 hours and the solid was isolated by filtration. The resulting solid was washed with chilled methanol (215 ml). The solid was dried under reduced pressure at 40 to 45° C. to obtain 127 g of pure (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate as a white solid.

Einzelnachweise

http://www.tradekorea.com/product/detail/P483269/Ticagrelor-intermediates---CAS-376608-71-8.html
https://en.wikipedia.org/wiki/Ticagrelor

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Upstream-Materialien And Downstream Produkte

Upstream-Materialien

(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid L-2-Hydroxy-2-phenylessigsure

Downstream Produkte

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 433)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Shanghai Safer Pharmaceutical Technology Co., Ltd.
021-31761238
sales@saferph.com CHINA 897 58
Shanghai Rochi Pharmaceutical Co.,Ltd.
21-38751876 +8615000076078
 info@rochipharma.com China 431 58
Jinan Finer Chemical Co., Ltd
+86-531-88989536 +86-15508631887
 sales@finerchem.com China 2967 58
Shanghai Jinli Pharmaceutical Co.,Ltd
+86-21-57256005 +86-15921811235
 chang@shjlchem.com China 20 58
Jiangsu Guotai Guomian Trading Co. Ltd.
+86-512-58916079 +86-13601562190
 pharmachem@gtgmt.com China 148 58
JUYE XIANDAI fine chemistry Co.,Ltd
+8618958038633
 tony@sdhypharma.com China 58 58
Hangzhou ICH Biofarm Co., Ltd 		+undefined8613073685410
 sales@ichemie.com China 985 58
Henan Fengda Chemical Co., Ltd 		+86-371-86557731 +86-13613820652
 info@fdachem.com China 7613 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806
 sales@capotchem.com China 29797 60
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886
info@dakenam.com China 15928 58
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaMine (2R)-Hydroxy(phenyl)ethanoate
  • (αR)-α-Hydroxybenzeneacetic Acid coMpd. with (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaMine
  • trans-(1R,2S)-2-(2,3-difluorophenyl)cyclopropylaMine Mandelat
  • (alphaR)-alpha-Hydroxybenzeneacetic acid compd. with (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine
  • (αR)-(1R,2S)-α-hydroxy-Benzeneacetic acid-coMpd.with 2-(3,4-difluorophenyl)cyclopropanaMine(1:1)
  • Ticagrelor InterMediate 4
  • (1R,2S)-2-(3,4-Difluorophenyl) cyclopropylamine D-Mandelate
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
  • Ticagrelor Intermediate3
  • (1S,2R)-2-(3,4-difluorophenyl)cyclopropan-1-amine (R)-2-hydroxy-2-phenylacetate
  • Benzeneacetic acid, α-hydroxy-, (αR)-(1R,2S)-coMpd. with 2-(3,4-difluorophenyl)cyclopropanaMine (1:1)
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropanaMine (R)-2-hydroxy-2-phenylacetate(1:1)
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropanaMine with (R)-(-)-Mandelic acid (1:1)
  • Benzeneaceticacid,a-hydroxy-,(R)-(1R,2S)-coMpd.with2-(3,4-difluorophenyl)cyclopropanaMine(1:1)
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaMiniuM(2R)-hydroxy(phenyl)
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaMiniuM (2
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropanaMine (S)-2-hydroxy-2-phenylacetate
  • (1R,2S)-2-(3,4-dimethylphenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate
  • (1R,2S)-2-(3,4-Difluorophenyl) cyclopropanaminium (2R)-hydroxy(phenyl)ethanoat
  • Trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine mandelate
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetic acid
  • (1S,2R)-2-(3,4- difluorophenyl)cyclopropan-1-amine hydrochloride
  • EX-7182
  • (1R-2R)-2-(3,4-diflrorophenyl)cyclopropanamine
  • (aR)-a-Hydroxy-benzeneacetic acid compd. with (1R,2S)-2-(3,4-difluorophenyl) cyclopropanamine (1:1)
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate 376608-71-8
  • (1R 2S)-2-(3 4-DIFUOROPHENYL)CYCLOPROPAN AMINIUM(2R)-HYDROXY(PHENYL)ETHANOATE
  • Ticagrelor int4
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropan-1-ammonium (2R)-2-hydroxy-2-phenylacetate
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaMine (2R)-Hydroxy(phenyl)etha
  • (1R,2S)-2-(3,4-Difluorophenyl)-cyclopropan-1-amine (2R)-2-hydroxy-2-phenylacetic acid
  • trans-(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-2-hydroxy-2-phenylethanoate
  • (1R,2S)-2-(3,4-DifL
  • )ethanoate, 98%
  • opropanaminium (2R)-hydroxy(phenyL
  • Ticagrelor Related Compound 107
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate ISO 9001：2015 REACH
  • 1-Acetyladamantane Intermediate，(1R,2S)-2-(3,4- Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
  • 2S)-2-(3
  • 4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
  • Ticagrelor side chain 2 mandelate
  • carboxylato(phenyl) methyl)holmium
  • trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine (2R)-2-hydroxy-2-phenylethanoate
  • (1R,2S)-2-(3,4-DIFLUOROPHENYL)CYCLOPROPANAMINE (2R) -2-HYDROXY-2-PHENYLACETATE
  • (1R,2R)-2-(3,4-difluorophenyl) cyclopropanamine(S)-(carboxyl...
  • Ticagrelor EP Impurity B
  • (1R,2R)-2-(3,4-difluorophenyl)cyclopropanamine(S)-(carboxylato(phenyl)methyl)holmium
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)ethanoate
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropanaMine (R)-2-hydroxy-2-phenylacetate
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine (R)-2-hydroxy-2-phenylacetate
  • (1R 2S)-2-(3 4- DIFLUOROPHENYL) CYCLOP ROPANAMINIUM (2R)- HYDROXY(PHENYL) ETHAN OATE MANDELIC ACID SALT
  • (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine D-Mandelic acid
  • Benzeneacetic acid, α-hydroxy-, (αR)-(1R,2S)-compd. with 2-(3,4-difluorophenyl)cyclopropanamine (1:1)
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate
  • Ticagrelor EP Impurity E (R)-Mandelate
  • (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)ethanoate (Ticagrelor Impurity)
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