HCID 67345213, compound → HCID 67349888, compound

HRID 1029031Notes

Reaction equation

HRID 1029031 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:27]([C:28]#[C:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1>C(O)C.CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:27]([CH2:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1

Participants

5

Reactant 1

HCID 67345213HCID 67345213, compound

Product 1

HCID 67349888HCID 67349888, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbut-1-ynyl)benzoate (655 mg, 1.477 mmol) in ethanol (30 mL) and EtOAc (5 mL) was added palladium on activated carbon (10% wt., 400 mg). The reaction mixture was evacuated and backfilled with nitrogen gas. The reaction mixture was evacuated and backfilled with hydrogen gas. The reaction mixture was allowed to stir overnight at RT. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated. Ethanol (10 mL) and palladium on activated carbon (10% wt., 500 mg) were added. The reaction mixture was evacuated and backfilled with hydrogen and allowed to stir overnight at RT. The reaction mixture was filtered through a pad of celite. The solvent was removed under reduced pressure and methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbutyl)benzoate was obtained as a yellow-tan residue and used in the next reaction without further purification.

Workup

  1. customThe reaction mixture was evacuated
  2. customThe reaction mixture was evacuated
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated
  5. additionEthanol (10 mL) and palladium on activated carbon (10% wt., 500 mg) were added
  6. customThe reaction mixture was evacuated
  7. stirringto stir overnight at RT
  8. filtrationThe reaction mixture was filtered through a pad of celite
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cba49b621978446d82c0d49fe4a44bdf
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…