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Trifluoroacetic acid → 2-{[4-(2-{[6-(4-Fluorophenyl)pyridazin-3-yl]oxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid

HRID 914327
Notes
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Reaction equation

HRID 914327 reaction equation
C([O:5][C:6](=[O:32])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[N:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:22]2[N:21]=[N:20][C:19]([O:18][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:32])=[O:5])[S:12][CH:13]=3)=[CH:24][CH:23]=2)=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597592532-{[4-(2-{[6-(4-Fluorophenyl)pyridazin-3-yl]oxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597590412-{[4-(2-{[6-(4-Fluorophenyl)pyridazin-3-yl]oxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{[4-(2-{[6-(4-Fluorophenyl)pyridazin-3-yl]oxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (400 mg) obtained in Example 123-2 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1) to give the title compound (290 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1)

Sources & evidence

ORD record
ord-7abe97031d014607b5382250aaaeaef6
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026370B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes