Trifluoroacetic acid → HCID 58899619, compound

HRID 2246627Notes

Reaction equation

HRID 2246627 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:10][C:11]([C:13]1[CH:14]=[C:15]([F:42])[C:16]([CH3:41])=[C:17]([C:19]2[CH:27]=[C:26]3[C:22]([C:23]([C:28]4[CH2:29][CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][CH:33]=4)=[N:24][NH:25]3)=[CH:21][CH:20]=2)[CH:18]=1)=[O:12])[CH3:9]>ClCCl>[CH2:8]([NH:10][C:11](=[O:12])[C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[C:26]3[C:22]([C:23]([C:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=4)=[N:24][NH:25]3)=[CH:21][CH:20]=2)[C:16]([CH3:41])=[C:15]([F:42])[CH:14]=1)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 588996041,1-dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate2×

Product 1

HCID 58899619HCID 58899619, compoundYield 2,908.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.73 ml) was added dropwise to a solution of 1,1-dimethylethyl 4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (Intermediate 20, 50 mg) in dichloromethane (10 ml) at room temperature under nitrogen then stirred at room temperature for 1 h. More trifluoroacetic acid (1.73 ml) was added and the mixture was stirred at room temperature under nitrogen for a further 1 h. The solvent was removed and the residue was dissolved in methanol and applied to an SCX ion exchange cartridge. Elution with a solution of ammonia (0.88) in methanol gave the title compound as a white solid (1.15 g).

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen for a further 1 h
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in methanol
  4. washElution with a solution of ammonia (0.88) in methanol

Sources & evidence

ORD record
ord-3105074f1caf4b44b0910dd006dc5552
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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