Ammonia → 4-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

HRID 1172505ノート

反応式

HRID 1172505 の反応式
[NH3:1].Cl[CH2:3][CH2:4][N:5]([CH2:28][CH2:29]Cl)[C:6]1[CH:26]=[C:25]([Cl:27])[C:9]2[O:10][C:11]3[C:20]([CH3:21])=[CH:19][C:18]([C:22]([OH:24])=[O:23])=[CH:17][C:12]=3[S:13](=[O:16])(=[O:15])[CH2:14][C:8]=2[CH:7]=1.[CH3:31]O>>[CH3:31][O:24][C:22]([C:18]1[CH:19]=[C:20]([CH3:21])[C:11]2[O:10][C:9]3[C:25]([Cl:27])=[CH:26][C:6]([N:5]4[CH2:4][CH2:3][NH:1][CH2:29][CH2:28]4)=[CH:7][C:8]=3[CH2:14][S:13](=[O:15])(=[O:16])[C:12]=2[CH:17]=1)=[O:23]

参加物

4

反応物 3

HCID 222AmmoniaHCID 887MethanolHCID 1317284742-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

生成物 1

HCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

反応条件

温度
110 °C

実験手順

Aqueous ammonia solution (30%, 4 mL) was added to a solution of Example 102j (0.5 g, 1.04 mmol) in methanol (1 mL), in an atmosphere of nitrogen, sealed in a pressure reactor vessel and heated at 110° C. for 6 h. The reaction mixture was brought to room temperature, concentrated, treated with chilled water and dilute HCl to neutral pH. The solid that precipitated was filtered, washed with water and dried. It was treated with methanolic HCl solution and stirred at 70° C. for 2.5 h. The reaction mixture was cooled and the solid that separated was filtered, washed with methanol, dried and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound as an off white solid. Yield: 0.220 g (48.24%); 1H NMR (DMSO-d6): δ 2.30 (m, 4H, 2CH2), 2.70 (s, 3H, CH3), 3.10 (m, 4H, 2CH2), 3.95 (s, 3H, OCH3), 5.10 (s, 2H, CH2), 7.10 (s, 1H, Ar), 7.20 (s, 1H, Ar), 8.05 (s, 1H, Ar) 8.20 (s, 1H, Ar): MS: m/e (ES+) 422 (M+1).

後処理

  1. customsealed in a pressure reactor vessel
  2. customwas brought to room temperature
  3. concentrationconcentrated
  4. additiontreated with chilled water and dilute HCl to neutral pH
  5. customThe solid that precipitated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. additionIt was treated with methanolic HCl solution
  10. temperatureThe reaction mixture was cooled
  11. customthe solid that separated
  12. filtrationwas filtered
  13. washwashed with methanol
  14. customdried
  15. custompurified

出典と根拠

ORDレコード
ord-a99dbbbcf49947198f28e46d00d97592
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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