4-Ethylphenyl isocyanate → 2-[3-(4-Ethyl-phenyl)-ureidomethyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide

HRID 1009205Notes

Reaction equation

HRID 1009205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH2:19])[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1)[CH3:21]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH:19][C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([CH2:20][CH3:21])=[CH:23][CH:24]=3)=[O:30])[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 900074-Ethylphenyl isocyanateHCID 577870612-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide

Product 1

HCID 114959512-[3-(4-Ethyl-phenyl)-ureidomethyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amideYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide (50 mg, 0.17 mmol) was dissolved in DMF (1 mL). 4-Ethyl phenylisocyanate (0.05 mL, 0.34 mmol) was added and the reaction mixture stirred at ambient temperature for 20 hours. The crude product was concentrated in vacuo. The product was purified by column chromatography (silica, 5% MeOH in DCM) to give a white solid (33.4 mg, 44%). 1H NMR (400 MHz, CD3OD): 8.07 (s, 1H), 7.26 (m, 4H), 7.19 (m, 2H), 7.11 (m, 2H), 4.66 (s, 2H), 3.60 (t, 2H), 2.90 (t, 2H), 2.58 (q, 2H), 1.20 (t, 3H); MS (ESI-LCMS) for C22H24C1N4O2S: 443 (MH+).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. customThe product was purified by column chromatography (silica, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-464f2dd8072e4cf0a90bf01c2375eacc
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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