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

HRID 1522269Notes

Reaction equation

HRID 1522269 reaction equation
Br[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.[CH2:27]([N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:48](Cl)(=O)[CH:49]=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:48]=[CH2:49])[CH:17]([CH2:16][CH2:15]3)[CH2:18]2)[C:2]=1[C:37]1[CH:36]=[N:35][N:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:38]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 53487663Tert-butyl 3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 867218481-(3-(((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)methyl)-8-azabicyclo[3.2.1]octan-8-yl)prop-2-en-1-one

Procedure

1-(3-(((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)methyl)-8-azabicyclo[3.2.1]octan-8-yl)prop-2-en-1-one was prepared from 5-bromo-6-chloropyrimidin-4-amine, tert-butyl 3-(aminomethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate, 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods B, C, D, and F. HPLC: 99%. MS: m/z=444 [M+H]+.

Sources & evidence

ORD record
ord-5f99c94bc6954c76b1756fbf975dd6ab
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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