3-Aminophenol → HCID 86721816, compound

HRID 1522230Notes

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:40]=[CH:39][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27](B3OC(C)(C)C(C)(C)O3)=[CH:26][N:25]=2)=[CH:21][CH:20]=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:27]1[CH:26]=[N:25][C:24]([O:23][C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:40][CH:39]=2)=[CH:29][CH:28]=1

Participants

Reactant 4

HCID 115683-Aminophenol

HCID 13140Acryloyl chloride

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

HCID 71092939HCID 71092939, compound

Product 1

HCID 86721816HCID 86721816, compound

Procedure

N-(3-((6-amino-5-(6-(4-fluorophenoxy)pyridin-3-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 2-(4-fluorophenoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, and acryloyl chloride using methods A, C, and F. HPLC: 99%. MS: m/z=444 [M+H]+. 1H-NMR (DMSO-D6) δ 10.17 (s, 1H), 8.09 (d, 1H), 8.03 (s, 1H), 7.82 (d, 1H), 7.43 (s, 1H), 7.30 (d, 1H), 7.25-7.15 (m, 6H), 7.07 (d, 1H), 6.92-6.58 (m, 3H), 6.34 (dd, 1H), 6.18 (d, 1H), 5.70 (d, 1H).

Sources & evidence

ORD record: ord-1cf7c06022bb41e2ab1325368f0ba657
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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