Sodium Carbonate → HCID 71547489, compound

HRID 1184548Notes

Reaction equation

HRID 1184548 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+].Cl[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]=1>CS(C)=O>[F:32][C:31]([F:34])([F:33])[C:27]1[N:26]=[C:25]([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)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6023342-Chloro-6-(trifluoromethyl)pyridineHCID 43810901HCID 43810901, compound

Product 1

HCID 71547489HCID 71547489, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To (7S,8aS)-tert-butyl 7-aminohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (310 mg, 1.29 mmol) and sodium carbonate (0.26 g, 2.5 mmol) in dimethyl sulfoxide (1 mL) was added 2-chloro-6-(trifluoromethyl)pyridine (0.35 g, 1.93 mmol). The mixture was stirred at 100° C. for 3 days and then concentrated. The residue was purified by chromatography on silica gel (100% ethyl acetate) to provide the title compound. MS (ESI) m/z 387 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-f577f1bf56924fcfb765879b1eebe49b
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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