Trifluoroacetic acid → HCID 68161452, compound

HRID 2041752Notes

Reaction equation

HRID 2041752 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][CH:34]=[CH:33][N: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][CH:34]=[CH:33][N:32]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68184862HCID 68184862, compound

Product 1

HCID 68161452HCID 68161452, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (2-{4-[(2S,4R)-1-acetyl-2-methyl-4-(2-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-pyrazol-1-yl}ethyl)methylcarbamate (for a preparation see intermediate 60) (126 mg, 0.250 mmol) in dichloromethane (DCM) (2 mL) was treated at room temperature with trifluoroacetic acid (TFA) (500 μl, 6.49 mmol) and the resulting mixture was stirred at this temperature for 1.5 h then concentrated in vacuo. The residue was dissolved in MeOH (1 mL) 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-2-pyridinyl-1,2,3,4-tetrahydro-4-quinolinamine formate (93 mg, 0.206 mmol, 83% yield) as a cream solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (1 mL)
  3. custompurified by MDAP (modifier: formic acid)
  4. customthe solvent was removed under vacuo

Sources & evidence

ORD record
ord-d6127b2311784e99ac39b76e33eb3826
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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