1-Hydroxybenzotriazole hydrate → 1-[4-Chloro-2-(trifluoromethyl)phenyl]-5-[2-(dimethylamino)-2-oxoethyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide

HRID 238962

반응식

HRID 238962 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14](=[O:26])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH:10]=[C:9]2[CH2:27][C:28](O)=[O:29])=[C:4]([C:31]([F:34])([F:33])[F:32])[CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:46][NH:47][CH3:48].C1COCC1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH2:27][C:28]([N:47]([CH3:48])[CH3:46])=[O:29])=[CH:10][C:11]([C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[O:26])=[C:12]2[CH3:13])=[C:4]([C:31]([F:33])([F:32])[F:34])[CH:3]=1

참가 물질

6

반응물 3

HCID 27960291-Hydroxybenzotriazole hydrateHCID 22320367Dimethylamine tetrahydrofuranHCID 67376656(1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid

생성물 1

HCID 452791841-[4-Chloro-2-(trifluoromethyl)phenyl]-5-[2-(dimethylamino)-2-oxoethyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide수율 54%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the above (1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid (30 mg, 0.518 mmol) in DMF (0.58 mL), 1-hydroxybenzotriazole monohydrate (18 mg, 0.12 mmol) and hydrochloric acid 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide (23 mg, 0.12 mmol) were successively added, and the mixture was stirred at room temperature for 1 hour. Thereafter, a 2M dimethylamine/THF solution was added to the mixture, and the mixture was stirred overnight. After the reaction, it was diluted with ethyl acetate, and the organic layer was washed with 1M hydrochloric acid, water and saturated brine. Thereafter, it was dried with sodium sulfate, filtration was carried out, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (17 mg, 54%).

후처리

  1. stirringthe mixture was stirred overnight
  2. customAfter the reaction, it
  3. washthe organic layer was washed with 1M hydrochloric acid, water and saturated brine
  4. dry with materialThereafter, it was dried with sodium sulfate, filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-32ca8c75f39c49a292aee21de54de583
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642640B2

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