HCID 131734012, compound → Trifluoroacetic acid

HRID 713251Notes

Reaction equation

HRID 713251 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].C([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[N:18][C:19]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([C:37]4[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=4[F:44])=[O:36])[CH2:31][CH2:30]3)=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[Cl:43][C:41]1[CH:40]=[CH:39][C:38]([F:44])=[C:37]([C:35]([CH:32]2[CH2:33][CH2:34][N:29]([C:19]3[N:18]=[C:17]4[CH2:16][NH:15][CH2:24][CH2:23][C:22]4=[N:21][C:20]=3[NH:25][CH:26]([CH3:27])[CH3:28])[CH2:30][CH2:31]2)=[O:36])[CH:42]=1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

6

Reactant 1

HCID 131734012HCID 131734012, compound

Product 2

HCID 6422Trifluoroacetic acidYield 422.6%HCID 118159194HCID 118159194, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1-(6-benzyl-2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone TFA salt (48.9 mg, 0.077 mmol) and Pd(OH)2 on carbon (20 wt %, 5 mg, 0.036 mmol) in THF (384 μL) was stirred at rt under an atmosphere of hydrogen gas (balloon). After 3 h, the mixture was diluted with MeOH, filtered through a pad of Celite™, washing with MeOH, and concentrated to afford he title compound as its TFA salt (37.1 mg, 88%) as a yellow film, which was used without further purification. ESI-MS m/z [M+H]+ 432.3.

Workup

  1. filtrationfiltered through a pad of Celite™
  2. washwashing with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e10aeda913464974a1343ae6aecfad67
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…