M-Phenylenediamine → HCID 86721770, compound

HRID 1522162Notes

Reaction equation

HRID 1522162 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.[CH2:18]([N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:39](Cl)(=[O:42])[CH:40]=[CH2:41]>>[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:39](=[O:42])[CH:40]=[CH2:41])[CH:15]=[CH:14][CH:13]=2)[C:2]=1[C:28]1[CH:27]=[N:26][N:25]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:29]=1

Participants

5

Reactant 4

HCID 7935M-PhenylenediamineHCID 13140Acryloyl chlorideHCID 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 86721770HCID 86721770, compound

Procedure

N-(3-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, benzene-1,3-diamine, 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods H, C, and F. HPLC purity: 99%. MS: m/z=412 [M+H]+. 1H-NMR (DMSO-d6) δ 10.17 (s, 1H), 8.65 (s, 1H), 8.26 (s, 1H), 8.02 (s, 1H), 7.78 (s, 1H), 7.61 (s, 1H), 7.44-7.03 (m, 10H), 6.45 (dd, 1H), 6.26 (d, 1H), 5.76 (d, 1H), 5.39 (s, 2H).

Sources & evidence

ORD record
ord-c4f7e2e986a149b9ac2cecda912a8fbe
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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