Potassium Carbonate → HCID 19801821, compound

HRID 982362Notes

Reaction equation

[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[C:21](=[O:24])([O-])[O-].[K+].[K+].BrC[C:29]([C:31]1[N:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]2=[N:33][CH:32]=1)=O>CN(C)C=O>[ClH:1].[ClH:1].[N:33]1[CH:32]=[C:31]([CH2:29][C:21]([N:16]2[CH2:17][CH2:18][CH:13]([C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])=[CH:20][CH:19]=3)[CH2:14][CH2:15]2)=[O:24])[N:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension comprising 1.91 g (6.0 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride, 3.0 g of potassium carbonate and 40 ml of dimethylformamide was stirred at 80° C. for 1 h. After cooling to room temperature, 1.99 g of 3-bromoacetylimidazo[1,2-a]pyridine prepared in the above step (i) was added thereto and the mixture was stirred at room temperature for 6 h. The reaction mixture was filtered and the filtrate was concentrated to obtain a solid residue, which was then purified according to silica gel column chromatography (chloroform:methanol=96:4). The purified product was converted into its dihydrochloride with ethanolic hydrogen chloride and recrystallized from methanol/acetone to obtain 1.75 g (yield: 58%) of the intended compound.

Workup

temperatureAfter cooling to room temperature
additionwas added
stirringthe mixture was stirred at room temperature for 6 h
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
customto obtain a solid residue, which
customwas then purified
customrecrystallized from methanol/acetone

Sources & evidence

ORD record: ord-b3e9fd0e5dd341f9b205ff9774ca3f11
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04996215

Reaction notes

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