Trifluoroacetic acid → Methyl 3-(3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylamino)pyridin-2-yl)phenylcarbamoyl)benzylthio)propanoate

HRID 625391Notes

Reaction equation

HRID 625391 reaction equation
C(OC([N:8]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=1)[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[CH:20]=[C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][C:16]=2[NH:27][C:28]([C:30]2[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=2)[CH2:33][S:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[O:29])[CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C([O-])(O)=O.[Na+]>[N:21]1([C:19]2[CH:18]=[CH:17][C:16]([NH:27][C:28]([C:30]3[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=3)[CH2:33][S:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[O:29])=[C:15]([C:11]3[CH:10]=[C:9]([NH:8][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:53])([F:54])[F:52])[CH:46]=4)[CH:14]=[CH:13][N:12]=3)[CH:20]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66588055Methyl 3-(3-(2-(4-(tert-butoxycarbonyl(3-(trifluoromethyl)benzyl)amino)pyridin-2-yl)-4-(piperidin-1-yl)phenylcarbamoyl)-benzylthio)propanoate

Product 1

HCID 66586785Methyl 3-(3-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)-benzylamino)pyridin-2-yl)phenylcarbamoyl)benzylthio)propanoateYield 29%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Into a 50-mL round bottom flask, was placed a solution of methyl 3-(3-(2-(4-(tert-butoxycarbonyl(3-(trifluoromethyl)benzyl)amino)pyridin-2-yl)-4-(piperidin-1-yl)phenylcarbamoyl)-benzylthio)propanoate (800 mg, 1.05 mmol, 1.00 equiv) in dichloromethane (2 mL), and 2,2,2-trifluoroacetic acid (5 mL). The resulting solution was stirred for 3 h at room temperature. The reaction progress was monitored by LCMS. The resulting solution was diluted with 20 mL of NaHCO3 (aq), extracted with 3×50 mL of dichloromethane, and the organic layers combined. The resulting mixture was washed with 1×50 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether:ethyl acetate (5:1). The product was obtained as 200 mg (29%) of a yellow solid.

Workup

  1. customInto a 50-mL round bottom flask, was placed
  2. extractionextracted with 3×50 mL of dichloromethane
  3. washThe resulting mixture was washed with 1×50 mL of brine
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. washeluted with petroleum ether:ethyl acetate (5:1)

Sources & evidence

ORD record
ord-1a5338cf0f394351ad9d3dbd844f4aa7
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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