Acetic Anhydride → HCID 11454267, compound

HRID 13806Notes

Reaction equation

HRID 13806 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])[CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[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]([CH3:27])[C:4](=[O:28])[CH:3]=[C:2]3[NH:1][C:29](=[O:31])[CH3:30])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 112241864-Amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11454267HCID 11454267, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

The product of Example 4 (18 mg) was combined with pyridine (2 mL), acetic anhydride (0.2 mL), and DMAP (5 mg). The reaction was heated to 85° C. for 1 hr at which point LC/MS indicated significant imide formation. The reaction was concentrated and redissolved in 1,4-dioxane before adding aqueous 1 M NaOH (1 mL). After 15 hours at room temperature the reaction was diluted with EtOAc and washed with brine before drying (Na2SO4). The concentrated residue was purified by preparative TLC (silica gel) eluted with EtOAc affording the title compound. HPLC/MS: 471.9 (M+1), 473.9 (M+3); Rt=3.79 inn.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in 1,4-dioxane
  3. additionbefore adding aqueous 1 M NaOH (1 mL)
  4. additionAfter 15 hours at room temperature the reaction was diluted with EtOAc
  5. washwashed with brine
  6. dry with materialbefore drying (Na2SO4)
  7. customThe concentrated residue was purified by preparative TLC (silica gel)
  8. washeluted with EtOAc affording the title compound

Sources & evidence

ORD record
ord-2f9612072c794ace80003ea4bbf6189b
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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