Acetyl chloride → N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

HRID 13825Notes

Reaction equation

HRID 13825 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:4](=[O:31])[C:3]=1[CH3:32].[H-].[Na+].[C:35](Cl)(=[O:37])[CH3:36]>C1COCC1.CCOC(C)=O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[N:7][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:5]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:4](=[O:31])[C:3]([CH3:32])=[C:2]3[NH:1][C:35](=[O:37])[CH3:36])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 24758Sodium hydrideHCID 113751874-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11466703N-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-3-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of EXAMPLE 42 (28 mg) in THF (0.5 mL) at 0° C. was added NaH (5 mg, 60% dispersion in mineral oil). The reaction stirred 10 minutes before acetyl chloride (7 μL) was added. Two hours later an additional 20 μL portion of acetyl chloride was added and again after an additional 90 minutes. After an additional hour of reaction time the reaction was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and dried (Na2SO4). The concentrated residue was purified by preparative TLC on silica gel eluted with 70% EtOAc in hexane affording the title compound. HPLC/MS: 528.0 (M+1), 530.0 (M+3); Rt=4.27 min.

Workup

  1. additionwas added
  2. customAfter an additional hour of reaction time the reaction
  3. washwashed with saturated aqueous NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. customThe concentrated residue was purified by preparative TLC on silica gel
  6. washeluted with 70% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-a2bbbca5b4704590b956ca2167a03084
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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