Trifluoroacetic acid → HCID 68161455, compound

HRID 2041751Notes

Reaction equation

HRID 2041751 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21](C)[C:22](=[O:28])[O:23]C(C)(C)C)[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH:22]([OH:28])=[O:23].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][NH:21][CH3:22])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68184861HCID 68184861, compound

Product 1

HCID 68161455HCID 68161455, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (2-{4-[(2S,4R)-1-acetyl-2-methyl-4-(4-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-pyrazol-1-yl}ethyl)methylcarbamate (for a preparation see intermediate 59) (147 mg, 0.291 mmol) in dichloromethane (DCM) (3 mL) at room temperature under nitrogen was treated with trifluoroacetic acid (TFA) (0.449 mL, 5.83 mmol). The resulting mixture was stirred at this temperature for 2 h then concentrated in vacuo. The residue was co-evaporated with DCM then was dissolved in 1:1 MeOH:DMSO (1 ml×2) and purified by MDAP (modifier: formic acid). The desired fractions were combined and the solvent was removed under vacuo to give (2S,4R)-1-acetyl-2-methyl-6-{1-[2-(methylamino)ethyl]-1H-pyrazol-4-yl}-N-4-pyridinyl-1,2,3,4-tetrahydro-4-quinolinamine formate salt (60 mg, 0.133 mmol, 45.7% yield).

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. dissolutionthen was dissolved in 1:1 MeOH
  4. customDMSO (1 ml×2) and purified by MDAP (modifier: formic acid)
  5. customthe solvent was removed under vacuo

Sources & evidence

ORD record
ord-dcd127d868bc4bad8c22c37ee88e24bb
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

Loading…