Diisopropylethylamine → Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate

HRID 1900873Notes

Reaction equation

HRID 1900873 reaction equation
Cl.[NH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:24]([C:26]1[CH:36]=[CH:35][C:29]([C:30]([N:32]=[C:33]=[O:34])=[O:31])=[CH:28][CH:27]=1)#[N:25]>C(#N)C>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:32][C:33](=[O:34])[NH:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=2)=[O:31])=[CH:35][CH:36]=1)#[N:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 149137394-Cyanobenzoyl isocyanateHCID 18918265Methyl (4-aminophenoxy)acetate hydrochloride

Product 1

HCID 23370013Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetateYield 52.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Methyl 4-aminophenoxyacetate, hydrochloride salt (1.09 g), was dissolved, with warming, in acetonitrile (50 ml) containing diisopropylethylamine (0.86 ml). To this solution at ambient temperature was added gradually with stirring a solution of 4-cyanobenzoyl isocyanate (1 g, preparation described in Weikert, R. J. et al (1991), J. Med. Chem. 34, 1630) in acetonitrile (5 ml). The precipitated solid was crystallised from boiling acetonitrile to give methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate (930 mg) as an off-white solid: m.p. 214°-217° C.; NMR Spectrum (DMSO-d6) 3.70 (3H, s), 4.77 (2H, s), 6.94 (2H, d), 7.48 (2H, d), 8.02 (2H, d), 8.12 (2H, d), 10.49 (1H, s), 11.19 (1H, s); Mass Spectrum m/Z 354 (M+H)+.

Workup

  1. additionTo this solution at ambient temperature was added gradually
  2. customThe precipitated solid was crystallised

Sources & evidence

ORD record
ord-8135e09261b04ed7a509324ad1fabe8c
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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