Cyanogen Bromide → HCID 59752286, 화합물

HRID 73220노트

반응식

HRID 73220 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][C:9]=1[N:10]([C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18])[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[N:38]#[C:39]Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:16][CH2:15][N:14]([C:39]#[N:38])[CH2:13][CH2:12]1)[C:17]([CH:19]1[CH2:20][CH2:21][CH:22]([CH3:25])[CH2:23][CH2:24]1)=[O:18])=[O:4]

참가 물질

5

반응물 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 59752320HCID 59752320, 화합물

생성물 1

HCID 59752286HCID 59752286, 화합물수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-[(4-methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (197 mg, 0.45 mmol) in CH2Cl2 (4.5 mL) was treated with K2CO3 (93 mg, 0.67 mmol) and cyanogen bromide (100 mg, 0.94 mmol). The reaction mixture was stirred at room temperature for 1 hour and heated at reflux for 18 h. The mixture was cooled at room temperature and filtered on celite. The filtrat was washed with AcOH (1N) and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using (2% MeOH/CH2Cl2) to provide 3-[(1-cyano-piperidin-4-yl)-(4-methyl cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (154 mg, 74% yield) as pale yellow foam.

후처리

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. temperatureThe mixture was cooled at room temperature
  4. filtrationfiltered on celite
  5. washThe filtrat was washed with AcOH (1N) and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-88f418f04c29414384e70533ece102d9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829030B2

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