Diisopropylethylamine → HCID 57970147, compound

HRID 1666607Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH2:19][C@H:20]1[CH2:24][CH2:23][N:22]([C:25](=[O:38])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH2:21]1.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(O)CCC.CN1CCCC1=O>[CH:12]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([NH:19][C@H:20]3[CH2:24][CH2:23][N:22]([C:25](=[O:38])[CH2:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][C:34]([F:35])([F:36])[F:37])=[CH:31][CH:32]=4)[CH2:21]3)[N:11]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-chloro-4-cyclohexylquinazoline (0.25 g), 1-((S)-3-aminopyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone mono hydrochloride (0.49 g), N,N-diisopropylethylamine (0.52 mL), N-methylpyrrolidone (1.0 mL), and n-butanol (1.0 mL) was stirred at 130° C. for 24 h. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate) to obtain the title compound (0.21 g).

Workup

extractionthe mixture was extracted with chloroform
dry with materialThe organic layer was dried with anhydrous sodium sulfate
customthe desiccant was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate)

Sources & evidence

ORD record: ord-8fec0464ba02435684432e75f130eb83
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044068B2

Reaction notes

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