Pyrrolidine → HCID 67313348, compound

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]4=[N:22][CH:21]=3)[C:17]([C:30]#[N:31])=[CH:16][N:15]=2)[CH3:12])=[CH:7][CH:6]=1)=[O:4].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:29][C:28]1[C:23]2[N:24]([C:20]([C:18]3[C:17]([C:30]#[N:31])=[CH:16][N:15]=[C:14]([NH:13][C@H:11]([C:8]4[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:6][CH:7]=4)[CH3:12])[N:19]=3)=[CH:21][N:22]=2)[CH:25]=[CH:26][CH:27]=1

Participants

Procedure

20 mg of the compound [3-2] was dissolved in 0.4 mL of N,N-dimethylformamide, and 7 μL of pyrrolidine was added thereto. The reaction mixture was stirred for 30 minutes at room temperature, and then thereto was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography, to obtain 3 mg of 4-(8-methylimidazo[1,2-a]pyridin-3-yl)-2-({(1S)-1-[4-(pyrrolidin-1-ylacetyl) phenyl]ethyl}amino)pyrimidine-5-carbonitrile [3-3] (hereinafter, referred to as the compound [3-3]) as a colorless oily product.