Chlorophenyl isocyanate → Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024449Notes

Reaction equation

HRID 1024449 reaction equation
[CH3:1][CH:2]([CH3:25])[CH:3]([NH:8][C:9]([C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[N:15]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>C1COCC1>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:35])[NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[N:15]=[C:11]([C:9]([NH:8][CH:3]([CH:2]([CH3:25])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])=[O:10])[S:12][CH:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 52934823Methyl 2-(4-(4-(3-(2-chlorophenyl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl-2-(4-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 3, 170 mg) in THF (2 ml), 2-chlorophenyl isocyanate (94 mg) was added and reaction mixture was stirred for 16 hours. Organic solvent was concentrated obtained sticky solid, was purified by column chromatography (silica gel, EtOAc-petroleum ether) to obtain title compound as solid. Yield: 190 mg (76%). 1H NMR (DMSO-d6, 300 MHz): δ 9.58 (s, 1H), 8.80 (d, 1H), 8.34 (s, 1H), 8.31 (s, 1H), 8.17 (d, 1H), 8.05 (d, 2H), 7.58 (d, 2H), 7.46 (d, 1H), 7.32 (t, 1H), 7.05 (t, 1H), 4.38 (t, 1H), 3.68 (s, 3H), 2.32 (m, 1H), 0.98 (t, 6H).

Workup

  1. customreaction mixture
  2. concentrationOrganic solvent was concentrated
  3. customobtained sticky solid
  4. customwas purified by column chromatography (silica gel, EtOAc-petroleum ether)

Sources & evidence

ORD record
ord-9214938ba4964b7bb636ab4b5a5f78b1
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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