3-(Trifluoromethyl)phenyl isocyanate → Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoate

HRID 1024435Notes

Reaction equation

HRID 1024435 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)=[C:25]=[O:26]>C1COCC1>[CH3:22][CH:21]([CH3:23])[CH:16]([NH:15][C:13]([C:11]1[O:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:25]([NH:24][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=3)=[O:26])=[CH:3][CH:4]=2)=[CH:9][N:10]=1)=[O:14])[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 67150345Methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate2×

Product 1

HCID 52933905Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate (Intermediate 1, 150 mg) in THF (3 ml) was added 1-isocyanato-3-(trifluoromethyl)benzene (132 mg) and the mixture was stirred overnight at RT. The mixture was then concentrated, purified by column chromatography (EtOAc:Pet ether, 2:8) and crystallized in CHCl3/Pet ether to give the title compound. Yield: 210 mg (88%). 1HNMR (DMSO-d6, 300 MHz): δ 9.13 (s, 1H), 9.09 (s, 1H), 8.99 (d, 1H), 8.03 (d, 1H), 7.82 (s, 1H), 7.8 (d, 2H), 7.64 (d, 2H), 7.58 (dd, 1H), 7.55 (dd, 1H), 7.34 (m, 1H), 4.3, (m, 1H), 3.68 (s, 3H), 2.24 (m, 1H), 0.95 (d, 6H); MS (ES+) m/z 505 (M+1).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by column chromatography (EtOAc:Pet ether, 2:8)
  3. customcrystallized in CHCl3/Pet ether

Sources & evidence

ORD record
ord-b19295dcd2fc4cd5bf1b05203f1e8b83
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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