2-Amino-4-methylthiazole → HCID 54716318, compound

HRID 2232104Notes

Reaction equation

HRID 2232104 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:10]=1[C:25](OCC)=[O:26]>C1(C)C=CC=CC=1>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][C:10]=1[C:25]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1)=[O:26]

Participants

4

Reactant 2

HCID 741432-Amino-4-methylthiazoleHCID 85585358HCID 85585358, compound

Product 1

HCID 54716318HCID 54716318, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 14.5 g of 2-amino-4-methylthiazole and 25.0 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 250 ml of toluene was refluxed for 24 hours in a soxhlet apparatus containing 20 g of 4 Å molecular sieves. Evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel: 2% diethyl ether-dichloromethane as the eluent) followed by recrystallization from diethyl ether to yield 20.7 g (67%) of 1,2-dihydro-4-hydroxy-N-(4-methyl-2-thiazolyl)-1-phenyl-3-quinolinecarboxamide, m.p. 228°-230° C.

Workup

  1. additioncontaining 20 g of 4 Å molecular sieves
  2. customEvaporation of the volatiles
  3. customafforded a residue which
  4. customwas purified by means of high pressure liquid chromatography (silica gel
  5. custom2% diethyl ether-dichloromethane as the eluent) followed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-297cb9a230024ac1bdd9c0cce2934554
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

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