3-Aminophenol → HCID 71474541, compound

HRID 1522227Notes

Reaction equation

HRID 1522227 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]=[C:28]([S:32]([NH2:35])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=2)O1.[C:37](Cl)(=[O:40])[CH:38]=[CH2:39]>>[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:37](=[O:40])[CH:38]=[CH2:39])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([S:32](=[O:34])(=[O:33])[NH2:35])[CH:27]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 164142303-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamideHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474541HCID 71474541, compound

Procedure

N-(3-((6-amino-5-(3-sulfamoylphenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide, and acryloyl chloride using methods A, C, and F. HPLC: 98%. MS: m/z=412 [M+H]+. 1H-NMR (DMSO-D6) δ 10.17 (s, 1H), 8.04 (s, 1H), 7.79-7.75 (m, 2H), 7.61-7.58 (m, 2H), 7.43 (s, 1H), 7.32-7.30 (m, 3H), 7.23 (t, 1H), 6.77-6.52 (m, 3H), 6.34 (dd, 1H), 6.18 (d, 1H), 5.70 (d, 1H).

Sources & evidence

ORD record
ord-08c309226c59459c8a79932c0b7c13a9
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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