Acryloyl chloride → N-(1-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)cyclopentyl)acrylamide

HRID 1522124Notes

Reaction equation

HRID 1522124 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][C:12]1([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:16][CH2:15][CH2:14][CH2:13]1.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:41](Cl)(=O)[CH:42]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][C:12]2([NH:17][C:18](=[O:24])[CH:41]=[CH2:42])[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 16740809tert-butyl N-[1-(aminomethyl)cyclopentyl]carbamateHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721749N-(1-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)cyclopentyl)acrylamide

Procedure

N-(1-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)cyclopentyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl (1-(aminomethyl)cyclopentyl)carbamate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC purity: 99%. MS: m/z=430 [M+H]+.

Sources & evidence

ORD record
ord-dc152920b3794f30ab64c0c8df53576b
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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