Nitrogen → HCID 53329178, compound

HRID 1028993Notes

Reaction equation

HRID 1028993 reaction equation
N#N.[NH2:3][C:4]1[C:13]([C:14]2[CH2:15][CH2:16][O:17][CH2:18][CH:19]=2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[C:27]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])[CH:10]=2)[N:5]=1>CCO.[Pd]>[NH2:3][C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[C:27]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])[CH:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 67376680HCID 67376680, compound

Product 1

HCID 53329178HCID 53329178, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (10%) (0.051 g, 0.048 mmol) was added to a degassed (N2) solution of (2-(2-amino-3-(3,6-dihydro-2H-pyran-4-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone (0.020 g, 0.048 mmol) in EtOH (1.00 mL). The solution was degassed with H2 gas and then stirred under a balloon of H2 gas for 12 h. The reaction was degassed with N2 and then filtered through a pad of celite with EtOAc and concentrated. The crude material was purified by silica gel chromatography by eluting with 20:1 2M NH3 in MeOH/DCM to provide (2-(2-amino-3-(tetrahydro-2H-pyran-4-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone. MS (ESI, pos. ion) m/z: 416 (M+1).

Workup

  1. customThe solution was degassed with H2 gas
  2. customThe reaction was degassed with N2
  3. filtrationfiltered through a pad of celite with EtOAc
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography
  6. washby eluting with 20:1 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-3617cf57ace948b7a15669f6649ae4e6
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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