3-Aminophenol → HCID 71474584, compound

HRID 1522229Notes

Reaction equation

HRID 1522229 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][CH:38]=[CH:37][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=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:25]1[CH:24]=[N:23][C:22]([O:21][C:20]2[CH:37]=[CH:38][CH:39]=[CH:40][C:19]=2[F:18])=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092882HCID 71092882, compound

Product 1

HCID 71474584HCID 71474584, compound

Procedure

N-(3-((6-amino-5-(6-(2-fluorophenoxy)pyridin-3-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 2-(2-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 10.16 (s, 1H), 8.07 (s, 1H), 8.02 (s, 1H), 7.84 (d, 1H), 7.42 (s, 1H), 7.32-7.15 (m, 7H), 6.86-6.60 (m, 3H), 6.34 (dd, 1H), 6.18 (d, 1H), 5.69 (d, 1H).

Sources & evidence

ORD record
ord-09121e81b70b4b47892d5e2100434edf
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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