3-Aminophenol → HCID 86721819, compound

HRID 1522235Notes

Reaction equation

HRID 1522235 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.[CH2:18]([N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:39](Cl)(=[O:42])[CH:40]=[CH2:41]>>[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:39](=[O:42])[CH:40]=[CH2:41])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:28]1[CH:27]=[N:26][N:25]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:29]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721819HCID 86721819, compound

Procedure

N-(3-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=413 [M+H]+. 1H-NMR (DMSO-D6) δ 10.18 (s, 1H), 8.08 (s, 1H), 7.98 (s, 1H), 7.66 (s, 1H), 7.45 (s, 1H), 7.33 (t, 1H), 7.29-7.20 (m, 6H), 6.99-6.64 (m, 3H), 6.34 (dd, 1H), 6.18 (d, 1H), 5.70 (d, 1H), 5.30 (s, 2H).

Sources & evidence

ORD record
ord-7cfd61b7892245a29bc563030d7f810d
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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