Acryloyl chloride → 1-(3-(((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-8-azabicyclo[3.2.1]octan-8-yl)prop-2-en-1-one

HRID 1522149Notes

Reaction equation

HRID 1522149 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[CH2:18][CH:17]2[N:19]([C:20]([O:22]C(C)(C)C)=O)[CH:14]([CH2:15][CH2:16]2)[CH2:13]1.[O:27]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:43](Cl)(=O)[CH:44]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH:12]2[CH2:13][CH:14]3[N:19]([C:20](=[O:22])[CH:43]=[CH2:44])[CH:17]([CH2:16][CH2:15]3)[CH2:18]2)[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 53487663Tert-butyl 3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 714743361-(3-(((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-8-azabicyclo[3.2.1]octan-8-yl)prop-2-en-1-one

Procedure

1-(3-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-8-azabicyclo[3.2.1]octan-8-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC purity: 100%. MS: m/z=456 [M+H]+.

Sources & evidence

ORD record
ord-988b098dc5804f42811b24cbcb95e0a0
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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