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

HRID 1522255Notes

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.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][N:29]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)[CH:30]=2)O1.[C:43](Cl)(=[O:46])[CH:44]=[CH2:45]>>[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:43](=[O:46])[CH:44]=[CH2:45])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:27]=[N:28][N:29]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=2)[CH:30]=1

Participants

Reactant 4

HCID 115683-Aminophenol

HCID 13140Acryloyl chloride

HCID 242192625,6-Dichloro-pyrimidin-4-ylamine

HCID 710929904-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(3-trifluoromethyl-benzyl)-1H-pyrazole

Product 1

HCID 71473852N-(3-((6-amino-5-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide

Procedure

N-(3-((6-amino-5-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(3-(trifluoromethyl)benzyl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 98%. MS: m/z=481 [M+H]+. 1H-NMR (DMSO-d6) δ 10.20 (s, 1H), 8.20 (s, 1H), 8.00 (s, 1H), 7.75-7.29 (m, 8H), 6.93-6.58 (m, 3H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.49 (s, 2H).

Sources & evidence

ORD record: ord-3f263e2ff0f94a50a6737d6a64f2b10d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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