Acryloyl chloride → N-(5-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide

HRID 1522249Notes

Reaction equation

HRID 1522249 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.Cl.Cl.[NH2:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[N:17][CH:18]=1.[CH2:20]([N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:41](Cl)(=[O:44])[CH:42]=[CH2:43]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:19][C:15]2[CH:14]=[C:13]([NH:12][C:41](=[O:44])[CH:42]=[CH2:43])[CH:18]=[N:17][CH:16]=2)[C:2]=1[C:30]1[CH:29]=[N:28][N:27]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:31]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 228320653-Amino-5-hydroxypyridine dihydrochlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721831N-(5-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide

Procedure

N-(5-((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 5-aminopyridin-3-ol dihydrochloride, 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: 77%. MS: m/z=414 [M+H]+.

Sources & evidence

ORD record
ord-0cbbe2d56f374d3db457c82b94bade57
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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