Potassium Carbonate → HCID 59761164, compound

HRID 600546Notes

Reaction equation

HRID 600546 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][C@H:19]2[CH2:23][CH2:22][N:21]([CH3:24])[C:20]2=[O:25])[CH:17]=1)[C:5]([NH:7][C:8]1[CH:13]=[N:12][C:11]([CH3:14])=[CH:10][N:9]=1)=[O:6].[N:26]1([C:30]([C:32]2[CH:37]=[CH:36][C:35](F)=[C:34]([Cl:39])[CH:33]=2)=[O:31])[CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[N:26]1([C:30]([C:32]2[CH:37]=[CH:36][C:35]([O:1][C:2]3[CH:3]=[C:4]([CH:15]=[C:16]([O:18][C@H:19]4[CH2:23][CH2:22][N:21]([CH3:24])[C:20]4=[O:25])[CH:17]=3)[C:5]([NH:7][C:8]3[CH:13]=[N:12][C:11]([CH3:14])=[CH:10][N:9]=3)=[O:6])=[C:34]([Cl:39])[CH:33]=2)=[O:31])[CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59346868(Azetidin-1-yl)(3-chloro-4-fluorophenyl)methanoneHCID 597611393-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide2×

Product 1

HCID 59761164HCID 59761164, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide (Intermediate 18) (136 mg, 0.4 mmol), azetidin-1-yl-(3-chloro-4-fluoro-phenyl)methanone (CAS no. 863454-79-9) (128 mg, 0.6 mmol) and potassium carbonate (111 mg, 0.8 mmol) in DMA (5 mL) was stirred at 120° C. for 16 hours. The solution was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate (40 mL), washed with water (2×20 mL) and brine (10 mL), then dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified by chromatography on silica eluting with 0-4% methanol/DCM to afford the product (120 mg, 56%). m/z 536 (M+H)+.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (40 mL)
  3. washwashed with water (2×20 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by chromatography on silica eluting with 0-4% methanol/DCM

Sources & evidence

ORD record
ord-acb3a89d55b54ac09ac87b3029baec65
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

Loading…