HCID 90408541, compound → HCID 90408541, compound

HRID 594078Notes

Reaction equation

HRID 594078 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=3[CH3:20])[NH2:16])[CH:10]=[C:9]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:8]=2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[CH3:20][C:19]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[C:11]1[CH:12]=[C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[N:8]=[C:9]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:10]=1.[O:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=3[CH3:20])[NH2:16])[CH:10]=[C:9]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[N:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 90408541HCID 90408541, compound

Product 2

HCID 90408541HCID 90408541, compoundHCID 90408686HCID 90408686, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(2-(3,6-dihydro-2H-pyran-4-yl)-6-morpholinopyridin-4-yl)-4-methylaniline (1.0 equiv.) in degassed ethanol (0.09 M) was added Pd/C (0.1 equiv.) and the solution was stirred under a hydrogen balloon for 1 h. Upon completion, the solution was filtered through Celite, and the filtrate was concentrated to dryness to give 4-methyl-3-(2-morpholino-6-(tetrahydro-2H-pyran-4-yl)pyridin-4-yl)aniline as desired product in 87% yield. LCMS (m/z) (M+H)=354.3, Rt=0.42 min.

Workup

  1. filtrationUpon completion, the solution was filtered through Celite
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-f4e22638867e4357b6763771868908f3
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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