Potassium Carbonate → HCID 19801821、化合物

HRID 1646202ノート

反応式

HRID 1646202 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochlorideHCID 15718183HCID 15718183、化合物

生成物 1

HCID 19801821HCID 19801821、化合物収率 113.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

22.1 g of 3-acetylimidazo[1,2-a]pyridine was dissolved in 220 ml of acetic acid. 35.1 ml of a 30% hydrogen bromide/acetic acid solution was added dropwise to the solution at 0° C. Then 28.6 g of bromine was added dropwise thereto at 40° C. The mixture was stirred at 40° C. for 2 h and crystals thus formed were filtered. The crystals were dissolved in 100 ml of water. The solution was made alkaline with an excess of an aqueous sodium hydrogencarbonate solution and then extracted with ethyl acetate. The organic layer was concentrated and the obtained brown solid was purified according to silica gel column chromatography (eluted with ethyl acetate) to obtain 13.5 g (yield: 40%) of 3-bromoacetylimidazo[1,2-a]pyridine (yield: 40%) in the form of yellow crystals. ii) 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.

後処理

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

出典と根拠

ORDレコード
ord-ebcb8bab2b304dfbbcc6cff8f3323f44
出典データセット
uspto-grants-1993_01
特許番号
US05179095

反応ノート

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