Potassium Carbonate → HCID 69639794, compound

HRID 1296751Notes

Reaction equation

HRID 1296751 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.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31].C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[C:33]1([O:32][C:30](=[O:31])[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:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformate2×HCID 69491883N-[2-Amino-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-3,5-dimethoxy-4-methyl-benzamide

Product 1

HCID 69639794HCID 69639794, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of compound 1g (100 mg, 0.26 mmol), phenyl chloroformate (0.033 mL, 0.26 mmol) and potassium carbonate (72 mg, 0.52 mmol) in DCE (2 mL) was stirred at rt overnight. Additional phenyl chloroformate (0.015 mL, 0.13 mmol) was added and the reaction was stirred at rt for 24 h. The reaction was concentrated on a rotary evaporator and the residue purified by silica gel chromotagraphy (ethyl acetate) to afford compound 19a (157 mg, 100%).

Workup

  1. stirringthe reaction was stirred at rt for 24 h
  2. concentrationThe reaction was concentrated on a rotary evaporator
  3. customthe residue purified by silica gel chromotagraphy (ethyl acetate)

Sources & evidence

ORD record
ord-da91d9b56864488bad4c1d8899d96ca4
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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