Ammonia → 4-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

HRID 2473

반응식

HRID 2473 반응식
[F:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([S:25]([C:28]3[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C[N:40]1CCOCC1.ClC(OCC(C)C)=O.N>C1COCC1>[C:32]([C:31]1[CH:35]=[CH:36][C:28]([S:25]([N:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([C:6](=[O:7])[C:5]3[CH:37]=[CH:38][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:13][CH2:12]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])(=[O:26])=[O:27])=[CH:29][CH:30]=1)(=[O:33])[NH2:40]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 196899274-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid

생성물 1

HCID 196898484-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide수율 50.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol). After 15 minutes of stirring at room temperature, 28% liquid ammonia (0.5 ml) was added to the reaction solution which was cooled in an ice bath, followed by additional 10 minutes of stirring at room temperature. The reaction mixture was extracted with methylene chloride, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1) to obtain 32 mg (50.9%) of the title compound in the form of light yellow oil.

후처리

  1. temperatureIn an atmosphere of argon and with cooling in an ice bath
  2. temperaturewas cooled in an ice bath
  3. waitfollowed by additional 10 minutes
  4. stirringof stirring at room temperature
  5. extractionThe reaction mixture was extracted with methylene chloride
  6. dry with materialthe resulting organic layer was dried on anhydrous sodium carbonate
  7. customThereafter, the solvent was removed by evaporation
  8. customthe resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1)

출처 및 근거

ORD 기록
ord-b00834c08920492095e2fbe7b5a3d02d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728835

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