Potassium Iodide → Methyl 6-{[3-(2-methylbenzyloxy)-5-(5-methylisoxazol-3-ylmethoxy)benzoyl]amino}-3-pyridinecarboxylate

HRID 1373176Notes

Reaction equation

HRID 1373176 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][C:40]1[CH:44]=[C:43]([CH3:45])[O:42][N:41]=1>CC(C)=O.C(OCC)(=O)C>[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][O:21][C:19]1[CH:18]=[C:4]([CH:3]=[C:2]([O:1][CH2:39][C:40]2[CH:44]=[C:43]([CH3:45])[O:42][N:41]=2)[CH:20]=1)[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)=[O:6]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazole2×HCID 21074240HCID 21074240, compound

Product 1

HCID 21074230Methyl 6-{[3-(2-methylbenzyloxy)-5-(5-methylisoxazol-3-ylmethoxy)benzoyl]amino}-3-pyridinecarboxylateYield 135.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 6-{[3-hydroxy-5-(2-methylbenzyloxy)benzoyl]amino}-3-pyridinecarboxylate (150 mg, 0.38 mM), potassium iodide (13 mg, 0.08 mM) and potassium carbonate (56 mg, 0.41 mM) in acetone (3 ml) were heated to 55° C. and a solution of 3-chloromethyl-5-methyl isoxazole (55 mg, 0.421 mM) in acetone (2 ml) was added. The reaction was stirred for 1 hour at 55° C. and a further addition of 3-chloromethyl-5-methyl isoxazole (33 mg, 0.25 mM) in acetone (1 ml) was made. The reaction was stirred for 24 hours at 55° C. before being allowed to cool to ambient temperature. Ethyl acetate (15 ml) was added and the resulting mixture was washed with 1N aqueous HCl (10 ml), saturated aqueous sodium bicarbonate solution (10 ml) and water (10 ml). The solvent was removed under reduced pressure to give methyl 6{[3-(2-methylbenzyloxy)-5-(5-methylisoxazol-3-ylmethoxy)benzoyl]amino}-3-pyridinecarboxylate as a white solid (252 mg); H1 NMR δ (d6-DMSO) 2.24 (3H s) 2.26 (3H s) 3.85 (3H s) 5.08 (2H s) 5.15 (s 2H) 6.28–6.35 (1H m) 6.88 (1H s) 7.17–7.43 (7H, m), 8.29 (1H s), 8.9 (11H d). MS [MH]+488

Workup

  1. stirringThe reaction was stirred for 24 hours at 55° C.
  2. temperatureto cool to ambient temperature
  3. washthe resulting mixture was washed with 1N aqueous HCl (10 ml), saturated aqueous sodium bicarbonate solution (10 ml) and water (10 ml)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1b6f5e7eb62e49378662612334fe8270
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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