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 1172519ノート

反応式

HRID 1172519 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b605d3a6a5b44f988274a4da9577181
出典データセット
uspto-grants-2010_11
特許番号
US07834001B2

反応ノート

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