HCID 131734015, compound → Trifluoroacetic acid

HRID 713255Notes

Reaction equation

HRID 713255 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:30]3[CH2:35][CH2:34][CH:33]([O:36][C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=4[F:44])[CH2:32][CH2:31]3)=[C:20]([NH:25][CH2:26][CH:27]([F:29])[F:28])[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[F:29][CH:27]([F:28])[CH2:26][NH:25][C:20]1[N:21]=[C:22]2[CH2:23][CH2:24][NH:15][CH2:16][C:17]2=[N:18][C:19]=1[N:30]1[CH2:31][CH2:32][CH:33]([O:36][C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=2[F:44])[CH2:34][CH2:35]1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

5

Reactant 1

HCID 131734015HCID 131734015, compound

Product 2

HCID 6422Trifluoroacetic acidYield 88.4%HCID 118159266HCID 118159266, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-benzyl-N-(2,2-difluoroethyl)-3-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (152 mg, 0.241 mmol) and Pd(OH)2 on carbon (33.9 mg, 0.048 mmol) in THF (2.41 mL) was purged with and placed under hydrogen (balloon) atmosphere at room temperature for 2 h. The mixture was then filtered through Celite™ and concentrated to give the title compound as a TFA salt (115 mg, 0.213 mmol).

Workup

  1. filtrationThe mixture was then filtered through Celite™
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e56583f81b7347a2abb7360b598cf876
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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