Potassium Carbonate → 3-{[2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-methyl}-benzoic acid methyl ester

HRID 1296750Notes

Reaction equation

HRID 1296750 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.Br[CH2:30][O:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:40](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:30][O:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:40][NH:1][C:2]2[CH:22]=[C:21]([C:23]3[N:27]=[C:26]([CH3:28])[O:25][N:24]=3)[CH:20]=[CH:19][C:3]=2[CH2:4][NH:5][C:6](=[O:18])[C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=2)[CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12602681BromomethylbenzoateHCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 694915793-{[2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-methyl}-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of compound 1g (76 mg, 0.20 mmol), methyl-3-(bromomethylbenzoate (56 mg, 0.24 mmol) and potassium carbonate (55 mg, 0.40 mmol) in DMF (1 mL) was sealed in a pressure tube and heated at 80° C. overnight. The reaction mixture was diluted with water, and the resulting solid precipitate was recovered by filtration to give compound 16a. ESI-MS m/e 531.4 (M+1).

Workup

  1. customwas sealed in a pressure tube
  2. filtrationthe resulting solid precipitate was recovered by filtration

Sources & evidence

ORD record
ord-abdf0e93c08d41a98156faf7af925a60
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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