Triethylamine → 1-(2-Methoxy-phenyl)-3-{3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-urea

HRID 2119593Notes

Reaction equation

HRID 2119593 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[O:13])=[CH:10][N:11]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]=[C:30]=[O:31].CCN(CC)CC>CO>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30]([NH:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9]([C:12](=[O:13])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:10][N:11]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 23442547[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone hydrochloride

Product 1

HCID 234426401-(2-Methoxy-phenyl)-3-{3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-ureaYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12.5 mg (0.04 mmol) [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone hydrochloride, 7.6 mg (0.05 mmol) 2-Methoxyphenyl isocyanate and 39 ul NEt3 in 1 ml methanol was stirred for 16 h at room temperature. After evaporation to dryness the residue was taken up in 1.5 ml MeOH/formic acid 1/1 and subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of product fractions yielded 7.9 mg (47%) of the title compound.

Workup

  1. customAfter evaporation to dryness the residue
  2. customHPLC separation on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customEvaporation of product fractions

Sources & evidence

ORD record
ord-8a2a5b047cd84f01910febc32216e45c
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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