Water → 4-Chloro-6-methyl-2-[4-(3-nitro-benzyl)-piperazin-1-yl]-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1927507노트

반응식

HRID 1927507 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:43])[C:19]2[O:25][C:24]3[C:26]([Cl:39])=[CH:27][C:28]([N:30]4[CH2:35][CH2:34][N:33](C5CC5)[CH2:32][CH2:31]4)=[CH:29][C:23]=3[CH2:22][S:21](=[O:41])(=[O:40])[C:20]=2[CH:42]=1)=[O:15].C([BH3-])#N.[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:43])[C:19]2[O:25][C:24]3[C:26]([Cl:39])=[CH:27][C:28]([N:30]4[CH2:31][CH2:32][N:33]([CH2:7][C:6]5[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=5)[CH2:34][CH2:35]4)=[CH:29][C:23]=3[CH2:22][S:21](=[O:40])(=[O:41])[C:20]=2[CH:42]=1)=[O:15]

참가 물질

7

반응물 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 1317284884-Chloro-2-(4-cyclopropyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

생성물 1

HCID 1317284894-Chloro-6-methyl-2-[4-(3-nitro-benzyl)-piperazin-1-yl]-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 887Methanol용매

실험 절차

m-Nitrobenzaldehyde (0.456 g, 3.02 mmol) and titanium isopropoxide (1.23 mL, 4.12 mmol) were added to a solution of Example 125k (1.2 g, 2.75 mmol) in methanol (75 mL) and refluxed for 1.5 h. Sodium cyanoborohydride (0.188 g, 2.75 mmol) was then added to the reaction mixture at 30° C. and refluxed for 3 h. It was cooled, treated with water and filtered. The filtrate was extracted with chloroform. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 5% methanol/chloroform) to obtain the title compound. Yield: 0.74 g (48%); 1H NMR (CDCl3): δ 2.6 (t, 4H, 2CH2), 2.63 (s, 3H, CH3), 3.22 (t, 4H, 2CH2), 3.63 (s, 2H, CH2), 3.9 (s, 3H, OCH3), 5.2 (s, 2H, CH2), 6.73 (s, 1H, Ar), 6.9 (s, 1H, Ar), 7.5 (t, 1H, Ar), 7.7 (d, 1H, Ar), 8.1 (s, 1H, Ar), 8.15 (d, 1H, Ar), 8.25 (s, 1H, Ar), 8.45 (s, 1H, Ar); MS: m/e (ES+) 573 (M+1).

후처리

  1. temperaturerefluxed for 1.5 h
  2. temperaturerefluxed for 3 h
  3. temperatureIt was cooled
  4. filtrationfiltered
  5. extractionThe filtrate was extracted with chloroform
  6. washThe organic layer was washed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. custompurified

출처 및 근거

ORD 기록
ord-c7b4ec69320f4455a0ee36008cb20fc5
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183234B2

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