1-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one → 4,4-Diethyl-1-{3-[2-hydroxy-2-(7-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]-3-methylbutyl}-1,4-dihydrobenzo[d][1,3]oxazin-2-one

HRID 2223119Notes

Reaction equation

HRID 2223119 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:43])[CH2:21][NH:22][C:23]([CH3:42])([CH3:41])[CH2:24][CH2:25][N:26]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[C:29]([CH2:38][CH3:39])([CH2:36][CH3:37])[O:28][C:27]2=[O:40])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:38]([C:29]1([CH2:36][CH3:37])[O:28][C:27](=[O:40])[N:26]([CH2:25][CH2:24][C:23]([NH:22][CH2:21][CH:20]([OH:43])[C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:19])[NH:16]3)([CH3:41])[CH3:42])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]1=2)[CH3:39]

Participants

5

Reactant 2

HCID 210728131-{3-[2-(7-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 210728434,4-Diethyl-1-{3-[2-hydroxy-2-(7-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]-3-methylbutyl}-1,4-dihydrobenzo[d][1,3]oxazin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-{3-[2-(7-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4dihydrobenzo[d][1,3]oxazin-2-one (152 mg, 0.338 mmol) and Pd/C (10%) (40 mg) in MeOH (12 mL) is hydrogenated at room temperature (RT) and 1 bar hydrogen pressure for 4 hours. The catalyst is filtered off through CELITE® filter aid and washed with MeOH (5 mL). The organic phase is evaporated down, the residue is triturated with EtOAc and the precipitate formed is filtered off and dried in vacuo. Yield: 76 mg (46%); Rf=0.3 (silica gel, dichloromethane/MeOH/saturated aqueous ammonia 90:10:0.5); ESI-MS: [M+H]+=494.

Workup

  1. customis hydrogenated at room temperature
  2. customfor 4 hours
  3. filtrationThe catalyst is filtered off through CELITE®
  4. filtrationfilter aid
  5. washwashed with MeOH (5 mL)
  6. customThe organic phase is evaporated down
  7. customthe residue is triturated with EtOAc
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-8b8cd115871946738f35f7c4a79c77a1
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

Loading…