Thiazolidinedione → HCID 88215764、化合物

HRID 2269306ノート

反応式

HRID 2269306 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[O:16][CH3:17].N1CCCCC1.[S:32]1[CH2:36][C:35](=[O:37])[NH:34][C:33]1=[O:38]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:36]2[S:32][C:33](=[O:38])[NH:34][C:35]2=[O:37])=[CH:20][CH:19]=1)[O:16][CH3:17]

参加物

5

反応物 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 131723013HCID 131723013、化合物

生成物 1

HCID 88215764HCID 88215764、化合物収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The title compound of Example 16 (580 mg, 1.7 mmol), piperidine (30 mg, 0.34 mmol) and 2,4thiazolidinedione (405 mg, 3.4 mmol) were combined in ethanol (20 mL) and the resulting solution was refluxed overnight. The solvent was removed in vacuo and the residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1) plus 5% acetic acid, to afford the title compound as a solid (640 mg, 87%). mp 205-206° C. 1HNMR (300 MHz, DMSO-d6): δ2.0 (m, 2H), 2.3 (s, 3H), 2.4 (t, 2H), 3.1 (s, 3H), 4.2 (dd, 1H), 7.4 (m, 5H), 7.6 (d, 2H), 7.7 (s, 1H), 7.9 (m, 2H).

後処理

  1. temperaturethe resulting solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified on silica gel
  4. washeluting with hexane/ethyl acetate (3/1) plus 5% acetic acid

出典と根拠

ORDレコード
ord-062d933aebc141b686292e4e2ff5b687
出典データセット
uspto-grants-2001_12
特許番号
US06329408B1

反応ノート

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