| Identification | Back Directory | [Name]
1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)- | [CAS]
1022150-11-3 | [Synonyms]
Ibrutinib Impurity 47
Ibrutinib iMpurity Boc
Ibrutinib Intermediates
(R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-
3-[4-Amino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyrimidin-1-y...
N-Boc-Ibrutinib ( tert-Butyl-1-carboxyl Piperidine analog of Ibrutinib)
(R)-1-(1-Boc-3-piperidinyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-ca
(R)-3-[4-Amino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid
3-[4-Amino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-but
tert-butyl (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
(R)-tert-Butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
tert-butyl (R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate
3-[4-Amino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester
(R)-tert-Butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (N-1)
(R)-3-[4-Amino-3-(4-phenoxy-phenyl)-
pyrazolo[3,4-d]pyrimidin-1-yl]-
piperidine-1-carboxylic acid tert-butyl ester
Ibrutinib impurity 5/(R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylate
1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)- | [Molecular Formula]
C27H30N6O3 | [MDL Number]
MFCD28167899 | [MOL File]
1022150-11-3.mol | [Molecular Weight]
486.57 |
| Chemical Properties | Back Directory | [Boiling point ]
673.9±55.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
4.09±0.30(Predicted) | [color ]
White to Off-White | [InChIKey]
NTSAEGNFPKKRLX-LJQANCHMSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC[C@@H](N2C3C(C(C4=CC=C(OC5=CC=CC=C5)C=C4)=N2)=C(N)N=CN=3)C1 |
| Hazard Information | Back Directory | [Uses]
N-Boc-Ibrutinib is an impurity of Ibrutinib (I124970), which is a highly selective Bruton’s tyrosine kinase (Btk) irreversible inhibitor. | [Synthesis]
3-(4-phenoxyphenyl) lH-pyrazolo [3,4-d] pyrimidin-4-amine (1.14g, 3.76mmol)was dissolved DMF (30mL) in, and then the reaction solution was added (S)-tert-butyl 3-((methylsulfonyl) oxy) piperidine-1-carboxylate (4.2g, 15.04mmol), cesium carbonate(0.64mL, 8.21 mmol), 4- dimethylaminopyridine pyridine (3.67g, 11.28mmol). Was stirred at 90 ℃, the reaction was completed, distilled under reduced pressure of DMF, and extracted with dichloromethane (150mL × 3), brine (60mL), dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure, the crude product was silica gel column Analysis of separation and purification (methylene chloride /methanol (V / V) = 40/1), to give the product (R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (1.28 g, 70 percent).
| [References]
[1] Patent: WO2012/158795, 2012, A1. Location in patent: Page/Page column 76
[2] Patent: WO2013/191965, 2013, A1. Location in patent: Page/Page column 156
[3] Patent: WO2014/22569, 2014, A1. Location in patent: Page/Page column 50
[4] Patent: US8673925, 2014, B1. Location in patent: Page/Page column 201
[5] Patent: CN106146511, 2016, A. Location in patent: Paragraph 0150; 0151; 0152 |
|
|