Methanol → HCID 136121407, compound

HRID 2062260Notes

Reaction equation

HRID 2062260 reaction equation
N#N.[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@H:22]([NH:26]C(=O)[O-])[CH2:21]2)[C:17]2[C:12](=[CH:13][C:14]([CH3:30])=[CH:15][CH:16]=2)[N:11]=1.CO>CCOC(C)=O.[Pd]>[NH2:26][C@H:22]1[CH2:23][CH2:24][CH2:25][N:20]([C:18]2[C:17]3[C:12](=[CH:13][C:14]([CH3:30])=[CH:15][CH:16]=3)[N:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[OH:3])[N:19]=2)[CH2:21]1

Participants

6

Reactant 3

HCID 887MethanolHCID 947NitrogenHCID 136412252HCID 136412252, compound

Product 1

HCID 136121407HCID 136121407, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (175 mg, 10% weight Pd on carbon) was added to a round bottom flask and the flask was flushed with N2. To this flask was then added MeOH (10 mL). After purging the flask again with N2, (S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-ylcarbamate (1.75 g, 3.74 mmol) dissolved in EtOAc (60 mL) and MeOH (50 mL) was added. After flushing the flask 3 times with N2, and evacuating it under vacuum, H2 was passed through the vigorously stirring mixture for 4 h until hydrogenation was complete. The mixture was filtered through a pad of Celite. The filtrate was concentrated to afford 2-(4-((S)-3-aminopiperidin-1-yl)-7-methylquinazolin-2-yl)phenol (0.62 g, 50%). LC/MS: m/z 335.5 (M+H)+ at 1.50 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe flask was flushed with N2
  2. customTo this flask was
  3. customAfter flushing the flask 3 times with N2
  4. customevacuating it under vacuum, H2
  5. filtrationThe mixture was filtered through a pad of Celite
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-81d1ad2a654f416baf1c9a9485023901
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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