Isopropanol → Isopropyl 4-(acetylamino)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 13847Notes

Reaction equation

HRID 13847 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH:13]=2)[N:8]([CH3:30])[C:7](=[O:31])[C:6]=1[C:32](OC)=[O:33])(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH:42]([OH:45])([CH3:44])[CH3:43]>C1COCC1>[C:1]([NH:4][C:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH:13]=2)[N:8]([CH3:30])[C:7](=[O:31])[C:6]=1[C:32]([O:45][CH:42]([CH3:44])[CH3:43])=[O:33])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 10796Cesium carbonateHCID 11307094Methyl 4-(acetylamino)-6(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 11157227Isopropyl 4-(acetylamino)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To the product of EXAMPLE 91 (10 mg) in isopropanol (4 mL) and THF (1 mL) was added Cs2CO3 (10 mg). The reaction stirred for about 14 hours at 50° C. LC/MS indicated incomplete reaction and the solution was then heated to 90° C. in a pressure tube for three hours. The reaction was concentrated and then diluted with EtOAc. After washing with saturated aqueous NaHCO3 the solution was dried (Na2SO4). The concentrated residue was purified by preparative TLC on silica gel eluted with 5% methanol in CH2Cl2 affording the title compound. HPLC/MS: 558.0 (M+1), 560.0 (M+3); Rt=4.93 min.

Workup

  1. customreaction
  2. temperaturethe solution was then heated to 90° C. in a pressure tube for three hours
  3. concentrationThe reaction was concentrated
  4. additiondiluted with EtOAc
  5. washAfter washing with saturated aqueous NaHCO3 the solution
  6. dry with materialwas dried (Na2SO4)
  7. customThe concentrated residue was purified by preparative TLC on silica gel
  8. washeluted with 5% methanol in CH2Cl2 affording the title compound

Sources & evidence

ORD record
ord-e276df89ef4b4f2ba8932354fa11c89e
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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