Trifluoroacetic acid → HCID 58899623, compound

HRID 2246621Notes

Reaction equation

HRID 2246621 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH3:34])=[C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([C:21]4[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH:26]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([NH:3][C:4](=[O:5])[C:6]1[CH:7]=[CH:8][C:9]([CH3:34])=[C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=2)[CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58899602HCID 58899602, compound2×

Product 1

HCID 58899623HCID 58899623, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-2-methylphenyl}-1H-indazol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (Intermediate 14, 550 mg) in dichloromethane (10 ml) under nitrogen was treated dropwise with trifluoroacetic acid (0.89 ml) then stirred at room temperature for 2 h. More trifluoroacetic acid (0.89 ml) was added and stirring was continued for a further 1 h. The solvent was evaporated and the residue was dissolved in methanol and applied to an SCX ion exchange cartridge. Elution with a solution of aqueous ammonia (0.88) in methanol (10%) gave the title compound as a white solid (432 mg).

Workup

  1. stirringstirring
  2. waitwas continued for a further 1 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in methanol
  5. washElution with a solution of aqueous ammonia (0.88) in methanol (10%)

Sources & evidence

ORD record
ord-a744ecb007b3441588ee7e0cb36189eb
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

Loading…