HCID 118159311, compound → Trifluoroacetic acid

HRID 713249Notes

Reaction equation

HRID 713249 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].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]([O:35][C:36]4[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][C:37]=4[F:44])[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:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:36]=1[O:35][CH:32]1[CH2:31][CH2:30][N:29]([C:19]2[N:18]=[C:17]3[CH2:16][NH:15][CH2:24][CH2:23][C:22]3=[N:21][C:20]=2[NH:25][CH:26]([CH3:28])[CH3:27])[CH2:34][CH2:33]1)[C:40]#[N:41].[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

5

Reactant 1

HCID 118159311HCID 118159311, compound

Product 2

HCID 6422Trifluoroacetic acidYield 459.9%HCID 118159211HCID 118159211, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-((1-(6-benzyl-2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)oxy)-3-fluorobenzonitrile 2,2,2-trifluoroacetate (579 mg, 0.942 mmol) and Pd(OH)2 (20 wt % Pd (dry basis) on carbon, wet, Degussa Type E101 NEW, 198 mg, 0.283 mmol) in THF (10 mL) was stirred under H2 (1.899 mg, 0.942 mmol) at 23° C. for 4 h. The mixture was filtered, rinsed with THF, concentrated via rotary evaporation, and dried in vacuo to give the title compound as a TFA salt (494 mg, 100%) as a brown oil. ESI-MS m/z [M+H]+ 411.4.

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with THF
  3. concentrationconcentrated via rotary evaporation
  4. customdried in vacuo

Sources & evidence

ORD record
ord-eb364ad477ea4ffa98f37ec30077184d
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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