HCID 68107087, compound → HCID 68227032, compound

HRID 1186529Notes

Reaction equation

HRID 1186529 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)[C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[C:27]([O:31][C:32](=[O:43])[NH:33][CH2:34][CH2:35][CH:36]([NH2:42])[C:37]1[CH:41]=[CH:40][S:39][CH:38]=1)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32](=[O:43])[NH:33][CH2:34][CH2:35][CH:36]([NH:42][C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)[C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)[C:37]1[CH:41]=[CH:40][S:39][CH:38]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 68107087HCID 68107087, compoundHCID 682264863-(2-Methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine

Product 1

HCID 68227032HCID 68227032, compound

Conditions

Temperature
140 °C

Procedure

The mixture of 3-(2-methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 46 supra) (150 mg, 0.402 mmol) and (3-amino-3-thiophen-3-yl-propyl)-carbamic acid tert-butyl ester (from Example 69 supra) (412 mg, 1.608 mmol) was heated at 140° C. with stirring for 2 hours. The oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 20:1) to afford crude (3-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-3-thiophen-3-yl-propyl)-carbamic acid tert-butyl ester. (Yield 400 mg).

Workup

  1. customThe oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 20:1)

Sources & evidence

ORD record
ord-b85d602fb6bc405c9796f0fe7ba3e1a5
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

Loading…