benzyl((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate → 2-(4-((R)-3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 2062277Notes

Reaction equation

HRID 2062277 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[OH:35])[N:19]=2)[CH2:13]1)C1C=CC=CC=1>[Pd].CCO>[NH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[OH:35])[N:19]=2)[CH2:13]1

Participants

4

Reactant 1

HCID 136121492benzyl((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

Product 1

HCID 1361214762-(4-((R)-3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of benzyl((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (855 mg, 1.77 mmol) and EtOH (15 mL) in a round bottom flask was added Pd/C (86 mg, 10% wt Pd on carbon) and the flask was sealed with a septum. The atmosphere in the flask was evacuated, purged with N2, and equipped with a balloon charged with H2. The mixture was stirred under an H2 atmosphere at ambient pressure for 3 h. After filtration through a plug of Celite using MeOH as the eluting solvent, the reaction mixture was concentrated to 2-(4-((R)-3-(aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol (625 mg) as a yellow solid. LC/MS: m/z 349.3 (M+H)+ at 1.82 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe flask was sealed with a septum
  2. customThe atmosphere in the flask was evacuated
  3. custompurged with N2
  4. customequipped with a balloon
  5. additioncharged with H2
  6. filtrationAfter filtration through a plug of Celite
  7. concentrationthe reaction mixture was concentrated to 2-(4-((R)-3-(aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol (625 mg) as a yellow solid
  8. waitLC/MS: m/z 349.3 (M+H)+ at 1.82 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-594badc46acb408490aa5a130a333d6f
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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