Acryloyl chloride → N-(3-((6-amino-5-(6-phenoxypyridin-3-yl)pyrimidin-4-yl)oxy)-4-fluorophenyl)acrylamide

HRID 1522225Notes

Reaction equation

HRID 1522225 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]=[CH:13][C:14]([F:18])=[C:15]([OH:17])[CH:16]=1.[O:19]([C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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:15]2[CH:16]=[C:11]([NH:10][C:41](=[O:44])[CH:42]=[CH2:43])[CH:12]=[CH:13][C:14]=2[F:18])[C:2]=1[C:29]1[CH:28]=[N:27][C:26]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 223467202-Phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 226414135-Amino-2-fluorophenolHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474540N-(3-((6-amino-5-(6-phenoxypyridin-3-yl)pyrimidin-4-yl)oxy)-4-fluorophenyl)acrylamide

Procedure

N-(3-((6-amino-5-(6-phenoxypyridin-3-yl)pyrimidin-4-yl)oxy)-4-fluorophenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 5-amino-2-fluorophenol, 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=444 [M+H]+. 1H-NMR (DMSO-D6) δ 10.16 (s, 1H), 8.09 (s, 1H), 7.99 (s, 1H), 7.80 (d, 1H), 7.59 (d, 1H), 7.38-7.32 (m, 3H), 7.21-6.91 (m, 5H), 6.70 (broad s, 2H), 6.31 (dd, 1H), 6.18 (d, 1H), 5.69 (d, 1H).

Sources & evidence

ORD record
ord-5c6564b6b1b345679f7dfc5b09ed82ff
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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