Methanol → N-[3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

HRID 13837Notes

Reaction equation

HRID 13837 reaction equation
[C:1]([N:4]([C:8]1[C:17]2[C:12](=[N:13][C:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH:16]=2)[N:11]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:10](=[O:36])[C:9]=1[Cl:37])C(=O)C)(=[O:3])[CH3:2].CO.C1COCC1>C(N(CC)CC)C>[Cl:37][C:9]1[C:10](=[O:36])[N:11]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:12]2[C:17]([C:8]=1[NH:4][C:1](=[O:3])[CH3:2])=[CH:16][C:15]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[C:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:13]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11410345N-acetyl-N-(3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

Product 1

HCID 11168248N-[3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The product of EXAMPLE 69 (85 mg) was combined with methanol (7 mL), THF (4 mL) water (2 mL) and triethylamine (2 mL) at room temperature. After 1.5 hours the reaction was concentrated and the residue dissolved in EtOAc. The solution was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4). The concentrated residue was purified by flash chromatography on silica gel eluted with 0-50% EtOAc in hexane affording the title compound. HPLC/MS: 513.9 (M+I), 515.9 (M+3); Rt=4.05 min.

Workup

  1. concentrationAfter 1.5 hours the reaction was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe solution was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customThe concentrated residue was purified by flash chromatography on silica gel
  6. washeluted with 0-50% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-34c8236bfae743d2ab6c0e16a8b1bcc4
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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