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

HRID 1522244Notes

Reaction equation

HRID 1522244 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:20]=[C:21]([CH:37]=[C:38]([F:40])[CH:39]=1)[CH2:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1.[C:41](Cl)(=[O:44])[CH:42]=[CH2:43]>>[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:41](=[O:44])[CH:42]=[CH2:43])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:25]=[N:24][N:23]([CH2:22][C:21]2[CH:20]=[C:19]([F:18])[CH:39]=[C:38]([F:40])[CH:37]=2)[CH:27]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 867218271-(3,5-difluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 86721826N-(3-((6-amino-5-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide

Procedure

N-(3-((6-amino-5-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 1-(3,5-difluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=449 [M+H]+. 1H-NMR (DMSO-d6) δ 10.23 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H), 7.77 (s, 1H), 7.54 (s, 1H), 7.41 (d, 1H), 7.32 (t, 1H), 7.16 (t, 1H), 7.14-6.78 (m, 5H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.76 (d, 1H), 5.42 (s, 2H).

Sources & evidence

ORD record
ord-cda58fb951ab445587c6aa1013ee58e2
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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