3-Aminophenol → HCID 71474583, compound

HRID 1522228Notes

Reaction equation

HRID 1522228 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]([F:31])([F:30])[O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.[C:32](Cl)(=[O:35])[CH:33]=[CH2:34]>>[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:32](=[O:35])[CH:33]=[CH2:34])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([O:20][C:19]([F:31])([F:30])[F:18])[CH:26]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474583HCID 71474583, compound

Procedure

N-(3-((6-amino-5-(3-(trifluoromethoxy)phenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, (3-(trifluoromethoxy)phenyl)boronic acid, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=417 [M+H]+. 1H-NMR (DMSO-D6) δ 10.22 (s, 1H), 8.09 (s, 1H), 7.59 (t, 1H), 7.48-7.44 (m, 2H), 7.39-7.36 (m, 3H), 7.28 (t, 1H), 6.95-6.55 (m, 3H), 6.39 (dd, 1H), 6.23 (d, 1H), 5.75 (d, 1H).

Sources & evidence

ORD record
ord-adf0643d8375446bade366183e04aebc
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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