Trifluoroacetic acid → HCID 10302319, compound

HRID 2211671Notes

Reaction equation

HRID 2211671 reaction equation
[F:1][C:2]1[CH:45]=[CH:44][C:5]([CH2:6][NH:7][C:8]2[N:43]=[CH:42][CH:41]=[CH:40][C:9]=2[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[C:15]([O:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3C(OC(C)(C)C)=O)[CH:14]=2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[N:43]=[CH:42][CH:41]=[CH:40][C:9]=2[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:24])([F:25])[C:20]([F:21])([F:22])[F:23])=[C:15]([O:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][NH:29]3)[CH:14]=2)=[O:11])=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10211524HCID 10211524, compound

Product 1

HCID 10302319HCID 10302319, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Fluoro-benzylamino)-N-[3-(1-Boc-pyrrolidin-2-ylmethoxy)-4-pentafluoroethyl-phenyl]-nicotinamide (Example 43) was dissolved in CH2Cl2 (8 mL) and TFA (8 mL) was added. After stirring at RT for 70 min, the mixture was concentrated in vacuo, diluted with 2N NaOH and CH2Cl2. The layers were separated and the aqueous layer was back extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide an light pink-orange solid. M+H 539.5. Calc'd for C26H24F6N4O2: 538.2.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with 2N NaOH and CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous layer was back extracted with CH2Cl2
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide an light pink-orange solid

Sources & evidence

ORD record
ord-94cb5c7530fd4eec9d13b3a0fee649dd
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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