Sodium Carbonate → HCID 71547725, compound

HRID 1184552Notes

Reaction equation

HRID 1184552 reaction equation
[NH2:1][C@@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C@@H:4]2[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>CN(C)C=O.ClCCl>[F:37][C:25]([F:24])([F:36])[C:26]1[CH:27]=[C:28]([S:32]([NH:1][C@@H:2]2[CH2:17][N:5]3[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:9][C@@H:4]3[CH2:3]2)(=[O:33])=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 43810901HCID 43810901, compound

Product 1

HCID 71547725HCID 71547725, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of (7S,8aS)-tert-butyl 7-aminohexahydropyrrolo[1,2-a]-pyrazine-2(1H)-carboxylate (0.22 g, 0.92 mmol) in dimethylformamide/dichloromethane (1:5, 5 mL) was added sodium carbonate (0.166 g, 1.56 mmol) and 3-(trifluoromethyl)-benzene-1-sulfonyl chloride (0.315 g, 1.29 mmol). The mixture was stirred at room temperature for 18 hours and then concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1) to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.19 (m, 1H), 1.38 (s, 9H), 1.40 (m, 2H), 1.70 (m, 1H), 1.84 (m, 1H), 2.00 (m, 1H), 2.18 (m, 1H), 2.64 (m, 1H), 2.79 (m, 1H), 3.70 (m, 1H), 3.80-3.95 (m, 2H), 7.83 (m, 1H), 8.05 (m, 1H), 8.11 (m, 2H), 8.15 (m, 1H); MS (ESI) m/z 450 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-cf871bc3a94644f0af34fdc3a8138dde
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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