Potassium Carbonate → HCID 68430670, compound

HRID 2244029Notes

Reaction equation

HRID 2244029 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][CH2:9][C:10]2[N:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][CH:11]=2)=[C:6]([CH2:21][CH2:22][CH3:23])[C:5]=1[OH:24])(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([O:37][CH3:38])=[O:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl.CC(C)=O.Cl>[CH3:38][O:37][C:35](=[O:36])[C:34]1[CH:39]=[CH:40][CH:41]=[C:32]([NH:31][C:16]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][O:8][C:7]3[CH:19]=[CH:20][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:24])[C:6]=3[CH2:21][CH2:22][CH3:23])[N:15]=2)=[O:18])[CH:33]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 15614005HCID 15614005, compound

Product 1

HCID 68430670HCID 68430670, compoundYield 76.1%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Add one drop of dimethylformamide to a solution of 6-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridine-2-carboxylic acid (800 mg, 2.43 mmol) and oxalyl chloride (0.23 mL, 2.67 mmol) in dichloromethane (24 mL) (gas evolution), stir 1 hour. Add a solution of methyl 3-aminobenzoate (365 mg, 2.43 mmol) and potassium carbonate (671 mg, 4.86 mmol) in acetone (16 mL). Stir resultant mixture for 16 hours. Dilute with dichloromethane (100 mL) and 1N hydrochloric acid (100 mL). Extract aqueous phase with dichloromethane, wash combined organic phase with saturated sodium bicarbonate solution. Dry organic phase over sodium sulfate and condense under reduced pressure. Triturate the residue in 1:1 acetone/diethyl ether. Dissolve resultant solid in ethyl acetate and wash with saturated sodium bicarbonate (2×), Dry organic phase over sodium sulfate and condense under reduced pressure to afford the title compound as a white solid (856 mg, 1.85 mmol). MS (m/z): 463 (M+1).

Workup

  1. stirringStir resultant mixture for 16 hours
  2. washExtract aqueous phase with dichloromethane, wash
  3. customDry organic phase over sodium sulfate and condense under reduced pressure
  4. customTriturate the residue in 1:1 acetone/diethyl ether
  5. dissolutionDissolve resultant solid in ethyl acetate
  6. washwash with saturated sodium bicarbonate (2×), Dry organic phase over sodium sulfate and condense under reduced pressure

Sources & evidence

ORD record
ord-11c73efaa97b4e2cb8d3ab39570d7b18
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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