Potassium Carbonate → HCID 59761156, compound

HRID 600561Notes

Reaction equation

HRID 600561 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@H:13]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14]2=[O:19])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:21]1[N:22]=[CH:23][C:24]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[N:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:30][N:29]([CH3:31])[C:27]([C:24]1[N:25]=[CH:26][C:21]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@H:13]3[CH2:17][CH2:16][N:15]([CH3:18])[C:14]3=[O:19])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:22][CH:23]=1)=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamideHCID 59761136methyl 3-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2×

Product 1

HCID 59761156HCID 59761156, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 8) (530 mg, 2 mmol), 5-chloro-N,N-dimethyl-pyrazine-2-carboxamide (CAS no. 915949-00-7) (446 mg, 2.4 mmol) and potassium carbonate (552 mg, 4 mmol) in acetonitrile (15 mL) was stirred at 120° C. for 2 hours. The mixture was evaporated and the residue dissolved in ethyl acetate (30 mL), washed with water (2×10 mL) and brine (20 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica eluting with 50 to 100% ethyl acetate in isohexane to afford the product (772 mg, 93%). m/z 415 (M+H+).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (30 mL)
  3. washwashed with water (2×10 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica eluting with 50 to 100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-5d462734a1ee42718c14a020c1385958
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

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