Hydrochloric Acid → HCID 69206897, compound

HRID 30715Notes

Reaction equation

HRID 30715 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:35]=[CH:34][C:22]([CH2:23][C:24]3[S:25][CH:26]=[C:27]([C:29]([O:31]CC)=[O:30])[N:28]=3)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>O.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:35]=[CH:34][C:22]([CH2:23][C:24]3[S:25][CH:26]=[C:27]([C:29]([OH:31])=[O:30])[N:28]=3)=[CH:21][CH:20]=2)=[O:17])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69205647HCID 69205647, compound

Product 1

HCID 69206897HCID 69206897, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzyl]-1,3-thiazole-4-carboxylate (0.52 g), a 1N aqueous sodium hydroxide solution (2 mL), tetrahydrofuran (2 mL) and ethanol (2 mL) was stirred at 50° C. for 30 min. 1N Hydrochloric acid (2 mL) and water were added to the reaction mixture and the precipitated crystals were collected by filtration to give 2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl }amino)benzyl]-1,3-thiazole-4-carboxylic acid as colorless crystals (0.41 g, yield 80%). Recrystallization thereof from acetone-hexane gave colorless prism crystals. melting point: 226-227° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-66742aff40fb495e907caf35932bb704
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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