1,1-Dimethylethyl 4-(5-amino-2-pyrimidinyl)-1-piperazinecarboxylate → Tert-butyl 4-(5-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 2271564Notes

Reaction equation

HRID 2271564 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2Cl.[NH2:18][C:19]1[CH:20]=[N:21][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[N:23][CH:24]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:18][C:19]1[CH:24]=[N:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)=[N:21][CH:20]=1

Participants

3

Reactant 2

HCID 594643191,1-Dimethylethyl 4-(5-amino-2-pyrimidinyl)-1-piperazinecarboxylateHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 86692861Tert-butyl 4-(5-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)pyrimidin-2-yl)piperazine-1-carboxylateYield 39%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (311 mg, 1.0 mmol) was reacted with tert-butyl 4-(5-aminopyrimidin-2-yl)piperazine-1-carboxylate (419 mg, 1.5 mmol) to afford the desired product (215 mg, 39%) as a yellow solid. ESI MS m/z 553 [C26H29BrN6O3+H]+

Sources & evidence

ORD record
ord-5304313f7d1648a4b518f789fdb974be
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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