Acryloyl chloride → HCID 86721822, compound

HRID 1522240Notes

Reaction equation

HRID 1522240 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.[NH2:11][C:12]12[CH2:17][C:15]([NH:18][C:19](=[O:28])OCC3C=CC=CC=3)([CH2:16]1)[CH2:14][CH2:13]2.[O:29]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:45](Cl)(=O)[CH:46]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:11][C:12]23[CH2:16][C:15]([NH:18][C:19](=[O:28])[CH:45]=[CH2:46])([CH2:17]2)[CH2:14][CH2:13]3)[C:2]=1[C:33]1[CH:34]=[CH:35][C:30]([O:29][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 54595568benzyl N-{4-aminobicyclo[2.1.1]hexan-1-yl}carbamate hydrochloride

Product 1

HCID 86721822HCID 86721822, compound

Procedure

N-(4-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)bicyclo[2.1.1]hexan-1-yl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, benzyl (4-aminobicyclo[2.1.1]hexan-1-yl)carbamate hydrochloride, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, hydrogenation, and F. HPLC: 100%. MS: m/z=428 [M+H]+. 1H-NMR (DMSO-d6) δ 8.46 (s, 1H), 8.32 (s, 1H), 7.44 (t, 2H), 7.27-7.12 (m, 8H), 6.85 (broad s, 2H), 6.18 (dd, 1H), 6.04 (d, 1H), 5.54 (d, 1H), 1.99-1.94 (m, 4H), 1.85-1.81 (m, 4H).

Sources & evidence

ORD record
ord-22d3fca5c9884089aaa8d74fa953edb1
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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