Ethyl Acetate → N-{2-fluoro-5-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide

HRID 400528Notes

Reaction equation

HRID 400528 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:16][CH2:15][N:14]3[CH2:17][CH2:18][CH2:19][C@@H:13]3[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]([F:39])([F:38])[C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.C(OCC)(=O)C>CN(C)C=O.ClCCl>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([N:11]2[CH2:16][CH2:15][N:14]3[CH2:17][CH2:18][CH2:19][C@@H:13]3[CH2:12]2)=[O:10])=[CH:3][C:2]=1[NH:1][S:34]([C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([F:26])([F:38])[F:39])[CH:29]=1)(=[O:36])=[O:35]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66676376(R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone

Product 1

HCID 46852597N-{2-fluoro-5-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]phenyl}-3-(trifluoromethyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To (R)-(3-amino-4-fluorophenyl)(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone (79 mg, 0.3 mmol) and sodium carbonate (64 mg, 0.6 mmol) in N,N-dimethylformamide (1 mL) was added 3-(trifluoromethyl)benzene-1-sulfonyl chloride (88 mg, 0.36 mmol) in dichloromethane (1 mL), and the mixture was stirred at room temperature for 18 hours. Then ethyl acetate was added, and the mixture was washed with water (2×10 mL). The organic phase was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (methanol/dichloromethane=1:15) to give the titled compound: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.25 (m, 1H), 1.60-2.20 (m, 6H), 2.70-3.10 (m, 5H), 4.35-4.55 (m, 1H), 7.22 (m, 3H), 7.82 (m, 1H), 8.00 (m, 3H); MS (ESI) m/z 472 (M+H)+.

Workup

  1. washthe mixture was washed with water (2×10 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (methanol/dichloromethane=1:15)

Sources & evidence

ORD record
ord-fed06e5d6ed648269e9070e751775ac9
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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