Acryloyl chloride → N-[(1S,3R)-3-[[6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl]amino]cyclopentyl]prop-2-enamide

HRID 1522242Notes

Reaction equation

HRID 1522242 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[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:23])OC(C)(C)C)[CH2:12]1.[O:24]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:40](Cl)(=O)[CH:41]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][C@@H:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:23])[CH:40]=[CH2:41])[CH2:12]2)[C:2]=1[C:28]1[CH:29]=[CH:30][C:25]([O:24][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 517769401,1-Dimethylethyl N-[(1S,3R)-3-aminocyclopentyl]carbamate

Product 1

HCID 86721824N-[(1S,3R)-3-[[6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl]amino]cyclopentyl]prop-2-enamide

Procedure

N-(cis-3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)cyclopentyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl (cis-3-aminocyclopentyl)carbamate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC: 98%. MS: m/z=416 [M+H]+. 1H-NMR (DMSO-d6) δ 8.36 (s, 1H), 8.11 (d, 1H), 7.45 (t, 2H), 7.28-7.12 (m, 7H), 7.07-6.82 (m, 3H), 6.15 (dd, 1H), 6.04 (d, 1H), 5.56 (d, 1H), 4.43 (broad s, 1H), 3.96 (sextet, 1H), 2.22 (m, 1H), 1.90-1.80 (m, 2H), 1.68-1.43 (m, 3H).

Sources & evidence

ORD record
ord-148fe257447640128d8f8a2b744cb024
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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