3-Aminophenol → N-(3-((6-amino-5-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide

HRID 1522248Notes

Reaction equation

HRID 1522248 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[F:18][C:19]1[CH:39]=[CH:38][C:22]([CH2:23][N:24]2[CH:28]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=[N:25]2)=[CH:21][CH:20]=1.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:40](=[O:43])[CH:41]=[CH2:42])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:27]1[CH:26]=[N:25][N:24]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:39][CH:38]=2)[CH:28]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 676155581-(4-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 86721830N-(3-((6-amino-5-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide

Procedure

N-(3-((6-amino-5-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 1-(4-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 99%. MS: m/z=431 [M+H]+. 1H-NMR (DMSO-d6) δ 10.22 (s, 1H), 8.14 (s, 1H), 8.04 (s, 1H), 7.73 (s, 1H), 7.52 (s, 1H), 7.39-7.32 (m, 4H), 7.17 (t, 2H), 6.95-6.68 (m, 2.5H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.36 (s, 2H).

Sources & evidence

ORD record
ord-c48ad5082e504c02a44e73d9afc1b7cb
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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