3,3,3-Trifluoropropane-1-sulfonyl chloride → N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3, 3, 3-trifluoropropane-1-sulfonamide

HRID 1969600노트

반응식

HRID 1969600 반응식
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH:11]1[C:19]2[N:18]3[C:20]([CH:23]4[CH:27]([CH3:28])[CH2:26][CH:25]([NH2:29])[CH2:24]4)=[CH:21][N:22]=[C:17]3[CH:16]=[N:15][C:14]=2[NH:13][CH:12]=1>CN(C=O)C>[CH:11]1[C:19]2[N:18]3[C:20]([C@@H:23]4[C@H:27]([CH3:28])[CH2:26][C@H:25]([NH:29][S:5]([CH2:4][CH2:3][C:2]([F:10])([F:9])[F:1])(=[O:7])=[O:6])[CH2:24]4)=[CH:21][N:22]=[C:17]3[CH:16]=[N:15][C:14]=2[NH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 585571313-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine

생성물 1

HCID 67999398N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3, 3, 3-trifluoropropane-1-sulfonamide수율 5.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3,3,3-Trifluoropropane-1-sulfonyl chloride (0.194 g, 0.987 mmol, Matrix) was added dropwise to a solution of TEA (0.31 mL, 2.2 mmol) and 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentanamine (0.28 g, 1.1 mmol, Preparation #53) in DMF (10 mL). The resulting mixture was stirred at ambient temperature for about 144 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water (20 mL each). The layers are separated and the organic layer was washed with brine (30 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified by using General Procedure AA (Table 2, Method 9, Rt=17.7 min, or =negative) to give N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)-3,3,3-trifluoropropane-1-sulfonamide (0.021 g, 4.6%) as a white solid: LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z 416 (M+H)+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water (20 mL each)
  3. customThe layers are separated
  4. washthe organic layer was washed with brine (30 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe residue was purified

출처 및 근거

ORD 기록
ord-b4bdbc623644483dbe1fac7da067fe59
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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