Water → {4-[3-(2-Methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 1186497Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][N:7]=1.[C:19]([O:23][C:24](=[O:33])[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([NH2:32])[CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[C:19]([O:23][C:24](=[O:33])[NH:25][CH:26]1[CH2:27][CH2:28][CH:29]([NH:32][C:2]2[C:3]3[N:4]([C:8]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=4)=[CH:9][N:10]=3)[CH:5]=[CH:6][N:7]=2)[CH2:30][CH2:31]1)([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 8-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine (from Example 44 supra) (0.9 g, 3.24 mmol) in DMF (25 mL) was added trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.04 g, 4.86 mmol) followed by diisopropylethylamine (0.63 g, 4.86 mmol). The reaction mixture was stirred at 95° C. for 15 hours and the mixture was poured into water. The precipitate formed was filtered, and. the obtained solid was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1) to afford {4-[3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 1.23 g, 83.4%). LC-MS: [M+H]+ 456.

Workup

customThe precipitate formed
filtrationwas filtered
customthe obtained solid was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1)

Sources & evidence

ORD record: ord-44892cb5802b43fc95c61beb7922b795
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673905B2

Reaction notes

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