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 1867327Notes

Reaction equation

HRID 1867327 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-1,4-dihydrobenzo[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-363f586a46d5443aa0ae4c7eccde9d61
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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