Trifluoroacetic acid → {4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-yl}(1,3-thiazolidin-3-yl)methanone

HRID 1911814Notes

Reaction equation

HRID 1911814 reaction equation
CC(C)(OC([N:7]1[CH2:11][C@@H:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:21]=[C:20]([CH3:29])[CH:19]=3)[CH2:14][CH2:13]2)[CH2:9][C@H:8]1[C:30]([N:32]1[CH2:36][CH2:35][S:34][CH2:33]1)=[O:31])=O)C.FC(F)(F)C(O)=O>ClCCl>[CH3:29][C:20]1[CH:19]=[C:18]([N:15]2[CH2:16][CH2:17][N:12]([C@@H:10]3[CH2:11][NH:7][C@H:8]([C:30]([N:32]4[CH2:36][CH2:35][S:34][CH2:33]4)=[O:31])[CH2:9]3)[CH2:13][CH2:14]2)[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66996784HCID 66996784, compound

Product 1

HCID 11949652{4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-yl}(1,3-thiazolidin-3-yl)methanoneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{(2S,4S)-1-(1,1-Dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (25.45 g, synthesized according to the compound described in Example 222 of WO02/14271) was dissolved in dichloromethane (200 mL). Trifluoroacetic acid (50 mL) was added at room temperature, and the mixture was stirred for 19 hrs. The reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with chloroform. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a solid (19.28 g, yield 93%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogencarbonate solution
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d39306b076154a5a891a5cce26b19257
Source dataset
uspto-grants-2013_12
Patent number
US08604198B2

Reaction notes

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