Trifluoroacetic acid → HCID 68185419, compound

HRID 2366972Notes

Reaction equation

HRID 2366972 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH2:6][C@@H:5]1[CH3:42])(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[CH3:41][CH:39]([O:38][C:36](=[O:37])[NH:35][C@H:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:16][CH:15]=3)[CH:9]=2)[N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([CH3:42])[CH2:6]1)[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67196668HCID 67196668, compound

Product 1

HCID 68185419HCID 68185419, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[({4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)amino]-1-piperidinecarboxylate (for a preparation see Intermediate 109) (605 mg, 1.045 mmol) in dichloromethane (DCM) (5 mL) was treated with TFA (1 mL, 12.98 mmol) and the resulting mixture was stirred at room temperature for 1.5 h then concentrated in vacuo. The residue was loaded on a 20 G SCX column and eluted with MeOH then with 2N NH3 in MeOH). The ammonia fractions were combined and concentrated in vacuo to give 1-methylethyl((2S,4R)-1-acetyl-2-methyl-6-{4-[(4-piperidinylamino)methyl]phenyl}-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (443 mg, 0.879 mmol, 84%) as a white glassy solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. washeluted with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd00e9c1978c4e87b265c1d0c3611226
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…