Trifluoroacetic acid → HCID 57955166, compound

HRID 73719Notes

Reaction equation

HRID 73719 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:47])[NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=4[F:46])=[C:29]([F:48])[CH:28]=3)[C:9]([CH2:24][O:25][CH3:26])=[C:10]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]2=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:43])[F:44])[CH:39]=[CH:38][C:37]=4[F:46])=[O:47])=[C:29]([F:48])[CH:28]=3)[C:9]([CH2:24][O:25][CH3:26])=[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66641290Tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate

Product 1

HCID 57955166HCID 57955166, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate was added methylene chloride (12.5 mL). To this suspension was added 12.5 mL of trifluoroacetic acid. The homogeneous solution was allowed to stir at rt under nitrogen for 17 hours. The reaction mixture was concentrated and the residue dissolved in EtOAc. The organic phase was washed with saturated sodium bicarbonate solution (2×), brine (1×), separated and the organic layer dried (Na2SO4). The organic layer was filtered, concentrated and left under vacuum overnight to yield the title compound (150 mg, 70.4% yield). 1H-NMR (DMSO-d6) MS [M+H]+=576; LCMS RT=2.51 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with saturated sodium bicarbonate solution (2×), brine (1×)
  4. customseparated
  5. dry with materialthe organic layer dried (Na2SO4)
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated
  8. waitleft under vacuum overnight

Sources & evidence

ORD record
ord-ec1b7fdcbc0347329428ad8086bd2f19
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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