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

HRID 13847
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HRID 13847 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e276df89ef4b4f2ba8932354fa11c89e
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728141B2

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