| Identification | Back Directory | [Name]
N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide | [CAS]
137973-76-3 | [Synonyms]
Dehydrotolvaptan
5-Dehydro Tolvaptan
Tolvaptan Intermediate
Tolvaptan 5-Oxo Analog
Tolvaptan impurity 5 (DM-21826)
7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-ox...
N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methy
N-[4-(7-chloro-5-oxo-3,4-dihydro-2H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine
N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbe
N-[4-(7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-Methylphenyl)-2-MethylbenzaMide
N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide
N-[4-[7-Chloro-2,3,4,5-Tetrahydro-5-oxo-1H-1-Benzazepine-1-yl)carbonyl]-3-MethylPhenyl]-2-MethylBenzamide
Benzamide, N-[4-[(7-chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methyl- | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C26H23ClN2O3 | [MDL Number]
MFCD19440797 | [MOL File]
137973-76-3.mol | [Molecular Weight]
446.93 |
| Chemical Properties | Back Directory | [Melting point ]
>118°C (dec.) | [Boiling point ]
593.2±50.0 °C(Predicted) | [density ]
1.307 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
12.97±0.70(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C26H23ClN2O3/c1-16-6-3-4-7-20(16)25(31)28-19-10-11-21(17(2)14-19)26(32)29-13-5-8-24(30)22-15-18(27)9-12-23(22)29/h3-4,6-7,9-12,14-15H,5,8,13H2,1-2H3,(H,28,31) | [InChIKey]
VENGMROMZOKURN-UHFFFAOYSA-N | [SMILES]
C(NC1=CC=C(C(N2C3=CC=C(Cl)C=C3C(=O)CCC2)=O)C(C)=C1)(=O)C1=CC=CC=C1C |
| Hazard Information | Back Directory | [Uses]
5-Dehydro Tolvaptan is an impurity of Tolvaptan (T536650), a selective, competitive arginine vasopressin V2 receptor antagonist used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH g | [Uses]
5-Dehydro Tolvaptan is an impurity of Tolvaptan (T536650), a selective, competitive arginine vasopressin V2 receptor antagonist
ngestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH). | [Preparation]
To a 3 L reactor was added 1- (4-amino-2-methylbenzoyl) -7-chloro-5-oxo-2,3,4,5-tetrahydro- 1 H- 1 -benzazepine (70. 0 g, 212.90 mmol), dichloromethane (560 ml) and distilled water (140 ml), and the mixture was stirred for 1 hour. Magnesium hydroxide (14.90 g, 14.90 mmol) was added to the reaction mixture at 10 ° C. or lower, and the mixture was stirred for 30 minutes. 2-Methylbenzoyl chloride (30.42 ml) was gradually added to the reaction mixture, stirring for 3 hours. The reaction mixture was filtered to remove magnesium hydroxide, and the pH of the reaction mixture was adjusted to pH 8 to 9 using an aqueous sodium hydroxide solution, and then the organic layer was separated. The obtained organic layer was dried with sodium sulfate (Na 2 SO 4), filtered, and concentrated under reduced pressure to give 5-Dehydro Tolvaptan (yield: 96 percent). | [Synthesis]
To a 3 L reactor was added 1-(4-amino-2-methylbenzoyl)-7-chloro-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one (70.0 g, 212.90 mmol), dichloromethane (560 mL), and distilled water (140 mL), and the reaction mixture was stirred for 1 hour. Magnesium hydroxide (14.90 g, 14.90 mmol) was slowly added to the reaction mixture at a temperature controlled below 10 °C and stirring was continued for 30 min. Subsequently, o-toluoyl chloride (30.42 mL) was slowly added dropwise and the reaction was continued with stirring for 3 hours after the dropwise addition. After completion of the reaction, the magnesium hydroxide was removed by filtration and the pH of the filtrate was adjusted to 8-9 with aqueous sodium hydroxide to separate the organic layer. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine 91.35 g in 96% yield. | [References]
[1] Patent: JP2018/12690, 2018, A. Location in patent: Paragraph 0029; 0030
[2] Patent: CN105315169, 2016, A. Location in patent: Paragraph 0170; 0224; 0225
[3] Patent: CN105753735, 2016, A. Location in patent: Paragraph 0181; 0217; 0218
[4] Patent: CN106883175, 2017, A. Location in patent: Paragraph 0017; 0018
[5] Patent: CN108503586, 2018, A. Location in patent: Paragraph 0044; 0045; 0054; 0055; 0056 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
parabiochem
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| Telephone: |
025-83453382-8005 |
| Website: |
www.parabiochem.cn |
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