Dichloromethane → HCID 67399604, compound

HRID 914400Notes

Reaction equation

HRID 914400 reaction equation
C([O:5][C:6](=[O:36])[C:7]([CH3:35])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][NH:17][C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)[N:21]=[C:20]([CH3:34])[CH:19]=2)[N:14]=1)[CH3:8])(C)(C)C.FC(F)(F)C(O)=O.[Cl:44]CCl>>[ClH:44].[CH3:35][C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][NH:17][C:18]2[N:22]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:31])([F:33])[F:32])=[CH:27][CH:28]=3)[N:21]=[C:20]([CH3:34])[CH:19]=2)[N:14]=1)([CH3:8])[C:6]([OH:36])=[O:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59759343HCID 59759343, compound

Product 1

HCID 67399604HCID 67399604, compound

Procedure

2-Methyl-2-({4-[2-({3-methyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester (690 mg) synthesized in Example 253-1 was dissolved in dichloromethane (4 mL), trifluoroacetic acid (4 mL) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1 to 1:1). The obtained compound was dissolved in diethyl ether (4 mL), 4 mol/L hydrochloric acid-ethyl acetate (0.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration to give the title compound (461 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=2:1 to 1:1)
  3. dissolutionThe obtained compound was dissolved in diethyl ether (4 mL)
  4. addition4 mol/L hydrochloric acid-ethyl acetate (0.5 mL) was added
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-99477acaa5cb41c99e9cb2d1b59e89d2
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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