HCID 131734046, compound → HCID 118159130, compound

HRID 713358Notes

Reaction equation

HRID 713358 reaction equation
OC(C(F)(F)F)=O.C([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[N:18][C:19]([NH:40][C@@H:41]([CH3:45])[CH2:42][O:43][CH3:44])=[C:20]([N:25]3[CH2:30][CH2:29][CH:28]([O:31][C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=4[F:39])[CH2:27][CH2:26]3)[N:21]=2)[CH2:16]1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[O:31][CH:28]1[CH2:27][CH2:26][N:25]([C:20]2[N:21]=[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]3=[N:18][C:19]=2[NH:40][C@@H:41]([CH3:45])[CH2:42][O:43][CH3:44])[CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 131734046HCID 131734046, compound

Product 1

HCID 118159130HCID 118159130, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-6-benzyl-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-(1-methoxypropan-2-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (127.7 mg, 0.200 mmol) in THF (2.00 mL) at room temperature was treated with Pd(OH)2 (20 wt %, 42.2 mg, 0.060 mmol). Hydrogen gas (balloon) was bubbled through the reaction mixture for 5 min. The vent needle was removed and the reaction mixture was stirred under hydrogen atmosphere for 1 h. The reaction mixture was opened to air and was filtered through a pad of Celite™, eluting with EtOAc and MeOH. The filtrate was concentrated under reduced pressure to give (S)-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-(1-methoxypropan-2-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine, as a TFA salt, as a yellow oil, which was carried forward without additional purification. ESI-MS m/z [M+H]+434.5.

Workup

  1. customHydrogen gas (balloon) was bubbled through the reaction mixture for 5 min
  2. customThe vent needle was removed
  3. filtrationwas filtered through a pad of Celite™
  4. washeluting with EtOAc and MeOH
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d98e7245d4641bc961424f28268e040
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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