Ethyl Acetate → Dimethyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2,4-quinolinedicarboxylate

HRID 2423398노트

반응식

HRID 2423398 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([C:22]([O:24][CH3:25])=[O:23])=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:27][C:28]1[C:29]([C:36]2[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=2[Cl:43])=[N:30][O:31][C:32]=1[CH:33]([CH3:35])[CH3:34].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:42][C:41]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:43])[C:36]=1[C:29]1[C:28]([CH2:27][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:17]=[C:16]4[C:11]([C:12]([C:22]([O:24][CH3:25])=[O:23])=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[N:15]4)=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[C:32]([CH:33]([CH3:35])[CH3:34])[O:31][N:30]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleHCID 136146135HCID 136146135, 화합물

생성물 1

HCID 59321483Dimethyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2,4-quinolinedicarboxylate수율 46.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 75 mg (0.22 mmol) of dimethyl 7-(4-hydroxyphenyl)-2,4-quinolinedicarboxylate, 135 mg (0.44 mmol) of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole and 125 mg (0.89 mmol) of K2CO3 in 2 mL DMF was stirred at ambient temperature for 60 hr. EtOAc was added and the mixture washed with three portions of H2O then brine. The solution was concentrated and the residue purified by silica gel chromatography (12 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes) to give 62 mg (46%) of dimethyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2,4-quinolinedicarboxylate as a clear glass. 1H NMR (400 MHz, CDCl3): δ 8.88 (d, J=9.0 Hz, 1H), 8.65 (s, 1H), 8.50 (s, 1H), 7.98 (d, J=9 Hz, 1H), 7.65 (d, J=9 Hz, 2H), 7.41 (d, J=8 Hz, 2H), 7.35-7.31 (m, 1H), 6.91 (d, J=9 Hz, 2H), 4.79 (s, 2H), 4.11 (s, 3H), 4.07 (s, 3H), 3.36 (septet, J=7 Hz, 1H), 1.44 (d, J=7 Hz, 6H). ESI-LCMS m/z 606 (M+H)+.

후처리

  1. washthe mixture washed with three portions of H2O
  2. concentrationThe solution was concentrated
  3. customthe residue purified by silica gel chromatography (12 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes)

출처 및 근거

ORD 기록
ord-7e644d0125824447872f94700c391078
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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