Trifluoroacetic acid → 2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochloride

HRID 914395Notes

Reaction equation

HRID 914395 reaction equation
C([O:5][C:6](=[O:33])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:22][N:21]=2)=O)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:32].[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:33])=[O:5])[S:12][CH:13]=3)=[N:21][CH:22]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673980322-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 673988412-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid hydrochlorideYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{[4-(2-{[5-(4-Chlorophenyl)pyridin-2-yl]amino}-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (145 mg) obtained in Example 242-3 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 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; chloroform:methanol=20:1). 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 (69 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; chloroform:methanol=20:1)
  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-a24a98fa14144d23b00a56d2ee93f354
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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