HCID 53329714, compound → HCID 67325503, compound

HRID 1029027Notes

Reaction equation

HRID 1029027 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=[CH:20][C:19]=3[C:30]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[CH:8]=2)[N:3]=1>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH2:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=[CH:20][C:19]=3[C:30]([N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)=[O:31])[CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 53329714HCID 53329714, compound

Product 1

HCID 67325503HCID 67325503, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbut-1-ynyl)phenyl)(pyrrolidin-1-yl)methanone (89 mg, 0.184 mmol, see Example 44) in ethanol (10 mL) was added palladium on activated carbon (10% wt; 150 mg). The reaction mixture was evacuated and backfilled with nitrogen gas. Then the reaction mixture was evacuated and backfilled with hydrogen gas. The reaction mixture was allowed to stir for 8 h at RT. The reaction mixture was filtered through a pad of celite. The solvent was removed under reduced pressure and the remaining residue was purified by column chromatography (10% MeOH in DCM). The titled compound was obtained as a light-yellow powder. MS (ESI, pos. ion) m/z: 487 (M+1).

Workup

  1. customThe reaction mixture was evacuated
  2. customThen the reaction mixture was evacuated
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. customThe solvent was removed under reduced pressure
  5. customthe remaining residue was purified by column chromatography (10% MeOH in DCM)

Sources & evidence

ORD record
ord-cba5cf29d9b3444fb989a23ae4e5c6e7
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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