Acryloyl chloride → 1-(4-(((6-Amino-5-(4-(phenylamino)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one

HRID 1522140Notes

Reaction equation

HRID 1522140 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[C:25]1([NH:31][C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:47](Cl)(=O)[CH:48]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18](=[O:20])[CH:47]=[CH2:48])[CH2:16][CH2:17]2)[C:2]=1[C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 22347219N-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)anilineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 714742811-(4-(((6-Amino-5-(4-(phenylamino)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one

Procedure

1-(4-(((6-amino-5-(4-(phenylamino)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, N-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, and acryloyl chloride using methods B, C, D, and F. HPLC purity: 98%. MS: m/z=429 [M+H]+.

Sources & evidence

ORD record
ord-f225d273bd5a41acadd2a59fcd29c875
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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