Acryloyl chloride → N-(5-((6-amino-5-(4-(4-cyanophenoxy)phenyl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide

HRID 1522257Notes

Reaction equation

HRID 1522257 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.CC1(C)C(C)(C)OB([C:28]2[CH:42]=[CH:41][C:31]([O:32][C:33]3[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=3)=[CH:30][CH:29]=2)O1.[C:44](Cl)(=[O:47])[CH:45]=[CH2:46]>>[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:44](=[O:47])[CH:45]=[CH2:46])[CH:18]=[N:17][CH:16]=2)[C:2]=1[C:28]1[CH:42]=[CH:41][C:31]([O:32][C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 223468894-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]benzonitrileHCID 228320653-Amino-5-hydroxypyridine dihydrochlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721838N-(5-((6-amino-5-(4-(4-cyanophenoxy)phenyl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide

Procedure

N-(5-((6-amino-5-(4-(4-cyanophenoxy)phenyl)pyrimidin-4-yl)oxy)pyridin-3-yl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 5-aminopyridin-3-ol dihydrochloride, 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods A, C, and F. HPLC: 98%. MS: m/z=452 [M+H]+. 1H-NMR (DMSO-d6) δ 10.48 (s, 1H), 8.57 (s, 1H), 8.12-8.09 (m, 2H), 7.97 (t, 1H), 7.86 (d, 2H), 7.52 (d, 2H), 7.23 (t, 4H), 6.43 (dd, 1H), 6.29 (d, 1H), 5.83 (d, 1H).

Sources & evidence

ORD record
ord-9b0691bc66964373b0f179006816241f
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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