HCID 66816087, compound → HCID 66816215, compound

HRID 1697103Notes

Reaction equation

HRID 1697103 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=2)[C:7]2[C:12]([C:13](=[O:22])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([CH3:23])[N:8]=2)=[O:4]>CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=2)[C:7]2[C:12]([C:13](=[O:22])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([CH3:23])[N:8]=2)=[O:4]

Participants

3

Reactant 1

HCID 66816087HCID 66816087, compound

Product 1

HCID 66816215HCID 66816215, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 104 (15 mg) was dissolved in EtOAc (10 mL) with Pc/C (10%, 5 mg), and hydrogenated using H2 (balloon) for 2 h. The product was filtered, concentrated, and purified by prep TLC (50/50 EtOAc/hexane), then 10% MeOH/DCM to provide 1-(3-amino-phenyl)-3-benzyl-7-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (Compound 105, 2.4 mg). M+H=478.

Workup

  1. customfor 2 h
  2. filtrationThe product was filtered
  3. concentrationconcentrated
  4. custompurified by prep TLC (50/50 EtOAc/hexane)

Sources & evidence

ORD record
ord-70de319fb2424a38ae6152258fa2d0b5
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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