Acryloyl chloride → HCID 86721823, compound

HRID 1522241Notes

Reaction equation

HRID 1522241 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19]C(C)(C)C)=O)[CH2:12]1.[CH2:24]([N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:45](Cl)(=O)[CH:46]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17](=[O:19])[CH:45]=[CH2:46])[CH2:12]2)[C:2]=1[C:34]1[CH:33]=[N:32][N:31]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:35]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721823HCID 86721823, compound

Procedure

(R)-1-(3-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (R)-tert-butyl 3-aminopiperidine-1-carboxylate, 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods B, C, D, and F. HPLC: 100%. MS: m/z=404 [M+H]+.

Sources & evidence

ORD record
ord-e31de79e1aa5481ca7a8dcc6288b4b57
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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