HCID 9953303, compound → HCID 9908764, compound

HRID 2415684Notes

Reaction equation

HRID 2415684 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([O:25][CH2:26][CH2:27][N:12]4[CH:11]=2)[CH:15]=[C:16]([C:21]#[C:22][CH2:23]O)[CH:17]=3)=[O:9])=[CH:4][CH:3]=1.[H][H]>[Pt].C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13]4=[C:14]([O:25][CH2:26][CH2:27][N:12]4[CH:11]=2)[CH:15]=[C:16]([CH2:21][CH2:22][CH3:23])[CH:17]=3)=[O:9])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 9953303HCID 9953303, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9908764HCID 9908764, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 50 mg of N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide of Preparation 12 and 20 mg of 5% platinum on carbon in 2 mL of 1:1 THF-methanol is stirred vigorously under 1 atmosphere of hydrogen gas for 3 hours, then filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure, and the residue chromatographed on silica using 2-3% methanol in dichloromethane. Following concentration under reduced pressure, the upper eluting fractions provide 16.5 mg of N-(4-chlorobenzyl)-7-oxo-9-propyl-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide (15B); the lower eluting fractions similarly afford 27.5 mg of N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide (15A).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue chromatographed on silica using 2-3% methanol in dichloromethane
  4. concentrationconcentration under reduced pressure
  5. washthe upper eluting fractions

Sources & evidence

ORD record
ord-0cc367a8d6c24a0684b72e45ce1bee55
Source dataset
uspto-grants-2004_11
Patent number
US06821969B2

Reaction notes

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