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Dimethylformamide → N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-3-cyano-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

HRID 13851
Notes
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Reaction equation

HRID 13851 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]([CH3:27])[C:4](=[O:28])[C:3]=1[C:29]#[N:30].[C:31](Cl)(=[O:33])[CH3:32].C(N([CH2:40][CH3:41])CC)C.CN(C=[O:46])C>C1COCC1.CCOC(C)=O>[C:31]([N: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:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH:10]=2)[N:5]([CH3:27])[C:4](=[O:28])[C:3]=1[C:29]#[N:30])[C:40](=[O:46])[CH3:41])(=[O:33])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 111902884-Amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile

Product 1

HCID 68713944N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-3-cyano-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of EXAMPLE 98 (43 mg) in DMF (0.5 mL) and THF (1 mL) was added acetyl chloride (65 μL) and triethylamine (0.13 mL). The reaction stirred about 4 hours at room temperature before it was diluted with EtOAc. The solution was washed with saturated aqueous NaHCO3 and brine. The solution was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-85% EtOAc in hexane affording N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-3-cyano-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridin-4-yl)acetamide which was subjected to the conditions of EXAMPLE 65 to afford the title compound. HPLC/MS: 496.8 (M+1), 498.8 (M+3); Rt=3.94 min.

Workup

  1. washThe solution was washed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel gradient
  5. washeluted with 0-85% EtOAc in hexane

Sources & evidence

ORD record
ord-b69949a2bce742e08d76265b860bdc44
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728141B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes