Potassium Carbonate → Methyl 3-[3'-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoate

HRID 250911Notes

Reaction equation

HRID 250911 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:35])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:35][N:26]([C:22]1[CH:21]=[C:20]([C:9]2[CH:10]=[CH:11][C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:13][C:8]=2[O:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:25]=[CH:24][CH:23]=1)[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 67273049HCID 67273049, compound

Product 1

HCID 67272943Methyl 3-[3'-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 500 μL (3.8 mmol, 3.8 eq) of 1-iodopentane and 400 mg (1.0 mmol, 1 eq) of methyl 3-[2-hydroxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate in 10 ml of methyl ethyl ketone in the presence of 500 mg (3.61 mmol, 3.6 eq) of potassium carbonate at 80° C. for 12 hours, methyl 3-[3′-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoate is obtained in oil form and is used in the following reaction without further purification.

Sources & evidence

ORD record
ord-be2324c43e314dd4a58fc5eb12a9d730
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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