3-Aminophenol → HCID 86721850, compound

HRID 1522272Notes

Reaction equation

HRID 1522272 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.[CH3:18][N:19]([CH3:41])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]2[CH:31]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:29]=[N:28]2)[CH:21]=1.[C:42](Cl)(=[O:45])[CH:43]=[CH2:44]>>[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:42](=[O:45])[CH:43]=[CH2:44])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:30]1[CH:29]=[N:28][N:27]([CH2:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([N:19]([CH3:41])[CH3:18])[CH:21]=2)[CH:31]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092852HCID 71092852, compound

Product 1

HCID 86721850HCID 86721850, compound

Procedure

N-(3-((6-amino-5-(1-(3-(dimethylamino)benzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, N,N-dimethyl-3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)aniline, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=456 [M+H]+. 1H-NMR (DMSO-d6) δ 10.20 (s, 1H), 8.11 (s, 1H), 7.99 (s, 1H), 7.71 (s, 1H), 7.49 (s, 1H), 7.41 (d, 1H), 7.31 (t, 1H), 7.12 (t, 1H), 6.80 (d, 1H), 6.64-6.56 (m, 5H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.76 (d, 1H), 5.28 (s, 2H), 2.83 (s, 6H).

Sources & evidence

ORD record
ord-9c7979b303b043b88eb3766cce5425ad
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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