Tert-butyl 4-[5-(2-aminopyrimidin-5-yl)pyridin-2-yl]piperazine-1-carboxylate → Tert-butyl 4-{5-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]pyridin-2-yl}piperazine-1-carboxylate

HRID 500173Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][N:3]=1.Cl[CH:28]([C:31]1([C:34]2[CH:35]=[C:36]3[C:41](=[CH:42][CH:43]=2)[N:40]=[CH:39][CH:38]=[CH:37]3)[CH2:33][CH2:32]1)[CH:29]=O>C(O)(C)C.CO>[N:40]1[C:41]2[C:36](=[CH:35][C:34]([C:31]3([C:28]4[N:7]5[CH:6]=[C:5]([C:8]6[CH:9]=[CH:10][C:11]([N:14]7[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]7)=[N:12][CH:13]=6)[CH:4]=[N:3][C:2]5=[N:1][CH:29]=4)[CH2:33][CH2:32]3)=[CH:43][CH:42]=2)[CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 4-[5-(2-aminopyrimidin-5-yl)pyridin-2-yl]piperazine-1-carboxylate (0.120 g, 0.337 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.0827 g, 0.337 mmol) in isopropyl alcohol (2.0 mL) was heated at 100° C. overnight. The mixture was diluted with methanol and purified by RP-HPLC (pH 10.0) to give the desired product (80 mg, 43.4%). LCMS: (M+H)=548.2.

Workup

custompurified by RP-HPLC (pH 10.0)

Sources & evidence

ORD record: ord-1877e47b1a354e5f90a16766ab6cd60e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

Loading…