3-Aminophenol → HCID 86721834, compound

HRID 1522251Notes

Reaction equation

HRID 1522251 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.[Cl:18][C:19]1[CH:20]=[C:21]([CH:37]=[CH:38][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:40](Cl)(=[O:43])[CH:41]=[CH2:42]>>[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:40](=[O:43])[CH:41]=[CH2:42])[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:37]=[CH:38][CH:39]=[C:19]([Cl:18])[CH:20]=2)[CH:27]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 86721835HCID 86721835, compound

Product 1

HCID 86721834HCID 86721834, compound

Procedure

N-(3-((6-amino-5-(1-(3-chlorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 1-(3-chlorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 99%. MS: m/z=447 [M+H]+. 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 8.18 (s, 1H), 8.03 (s, 1H), 7.75 (s, 1H), 7.52 (s, 1H), 7.42-7.26 (m, 6H), 6.96-6.65 (m, 2.6H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.76 (d, 1H), 5.39 (s, 2H).

Sources & evidence

ORD record
ord-c4104fac170f41c2b4aa1ee1d5d42b9d
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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