HCID 131734045, compound → Trifluoroacetic acid

HRID 713356Notes

Reaction equation

HRID 713356 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]([S:35]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=4)(=[O:37])=[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.[OH-].[OH-].[Pd+2]>[F:44][C:40]1[CH:39]=[C:38]([S: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]([CH3:28])[CH3:27])[CH2:30][CH2:31]2)(=[O:36])=[O:37])[CH:43]=[CH:42][CH:41]=1.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

5

Reactant 1

HCID 131734045HCID 131734045, compound

Product 2

HCID 6422Trifluoroacetic acidYield 475.4%HCID 118159219HCID 118159219, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-benzyl-3-(4-((3-fluorophenyl)sulfonyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (68 mg, 0.107 mmol) in THF (1333 μL) was added Pd(OH)2 (20 wt %, 22.5 mg, 0.032 mmol). The flask was purged with nitrogen then allowed to stir under an atmosphere of hydrogen (balloon) for 2 h. The reaction mixture was filtered through a hydrophilic PTFE 0.45 μm filter (Millipore® Millex-LCR) and washed with EtOAc. The crude material was concentrated in vacuo to give 3-(4-((3-fluorophenyl)sulfonyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine as a TFA salt (58 mg) as a yellow film.

Workup

  1. customThe flask was purged with nitrogen
  2. filtrationThe reaction mixture was filtered through a hydrophilic PTFE 0.45 μm
  3. filtrationfilter (Millipore® Millex-LCR)
  4. washwashed with EtOAc
  5. concentrationThe crude material was concentrated in vacuo

Sources & evidence

ORD record
ord-4e55c9f3145f4a23b908fa1d3265979e
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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