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 1969600Notes

Reaction equation

HRID 1969600 reaction equation
[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

Participants

4

Reactant 2

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

Product 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-sulfonamideYield 5.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-b4bdbc623644483dbe1fac7da067fe59
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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