M-Phenylenediamine → HCID 71474167, compound

HRID 1522108Notes

Reaction equation

HRID 1522108 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1.[O:18]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:16][C:12]2[CH:11]=[C:10]([NH:17][C:34](=[O:37])[CH:35]=[CH2:36])[CH:15]=[CH:14][CH:13]=2)[C:2]=1[C:22]1[CH:23]=[CH:24][C:19]([O:18][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 7935M-PhenylenediamineHCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474167HCID 71474167, compound

Procedure

N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, benzene-1,3-diamine, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods H, C, and F. HPLC purity: 100%. MS: m/z=424 [M+H]+. 1H-NMR (DMSO-d6), δ 10.11 (s, 1H), 8.47 (broad s, 1H), 8.22 (s, 1H), 7.67 (s, 1H), 7.31-6.97 (m, 14H), 6.37 (dd, 1H), 6.19 (d, 1H), 5.69 (d, 1H).

Sources & evidence

ORD record
ord-2e6c8a9b7dad4723b5684d2a50b248c8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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