HCID 22063465, compound → rac-8-(2-(1-(4-ethoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-6-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 12109Notes

Reaction equation

HRID 12109 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:36])[CH2:21][NH:22][C:23]([CH3:35])([CH3:34])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH3:33])=[CH:27][CH:26]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:23]([NH:22][CH2:21][CH:20]([C:11]2[C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=[C:9]([OH:8])[CH:10]=2)[OH:36])([CH3:35])[CH3:34])=[CH:26][CH:27]=1)[CH3:33]

Participants

4

Reactant 1

HCID 22063465HCID 22063465, compound

Product 1

HCID 11625493rac-8-(2-(1-(4-ethoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-6-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.5 g (2.8 mmol) of 6-benzyloxy-8-{2-[2-(4-ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one in 80 mL methanol are hydrogenated with 250 mg palladium on charcoal (10%) as catalyst at ambient temperature and normal pressure. The catalyst is suction filtered and the filtrate is evaporated down. The residue is dissolved in 5 mL ethanol by heating, seeded, and diluted with ethyl acetate. The solid precipitated is filtered off and washed. White solid. Yield 1.0 g (83%, hydrochloride); melting point: 232° C.-235° C.; mass spectrometry: [M+H]+=401.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. dissolutionThe residue is dissolved in 5 mL ethanol
  4. temperatureby heating
  5. additiondiluted with ethyl acetate
  6. customThe solid precipitated
  7. filtrationis filtered off
  8. washwashed

Sources & evidence

ORD record
ord-6c1e7ebe7ac64f5ca4ace310742af500
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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