HCID 131734002, compound → Trifluoroacetic acid

HRID 713229Notes

Reaction equation

HRID 713229 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]([NH:41][CH:42]([CH3:44])[CH3:43])=[C:20]([N:25]3[CH2:30][CH2:29][CH:28]([C:31]([C:33]4[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=4[F:40])=[O:32])[CH2:27][CH2:26]3)[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[Cl:39][C:37]1[CH:36]=[CH:35][C:34]([F:40])=[C:33]([C:31]([CH:28]2[CH2:29][CH2:30][N:25]([C:20]3[N:21]=[C:22]4[CH2:23][CH2:24][NH:15][CH2:16][C:17]4=[N:18][C:19]=3[NH:41][CH:42]([CH3:44])[CH3:43])[CH2:26][CH2:27]2)=[O:32])[CH:38]=1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

6

Reactant 1

HCID 131734002HCID 131734002, compound

Product 2

HCID 6422Trifluoroacetic acidYield 478.4%HCID 118159208HCID 118159208, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1-(6-benzyl-3-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone TFA salt (41.7 mg, 0.066 mmol) and Pd(OH)2 on carbon (20 wt %, 5 mg, 0.036 mmol) in THF (328 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 the title compound as its TFA salt (36 mg, 100%) 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-abd4b67086414cbdbade3af85eb3a1de
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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