Mesitylene → Edaglitazone

HRID 854417

反応式

HRID 854417 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][O:15][C:16]1[C:24]2[CH:23]=[CH:22][S:21][C:20]=2[C:19]([CH:25]=[C:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:18][CH:17]=1.N1C=C(C(O)=O)C=C(C(O)=O)C=1.C1(C)C=C(C)C=C(C)C=1.C(N(CC)CC)C>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][O:15][C:16]1[C:24]2[CH:23]=[CH:22][S:21][C:20]=2[C:19]([CH2:25][CH:26]2[S:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 7947MesityleneHCID 8471TriethylamineHCID 103663,5-Pyridinedicarboxylic acidHCID 853192475-[[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione

生成物 1

HCID 9825701Edaglitazone収率 92.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
167 °C

実験手順

A 2.5 l, 4-necked glass flask equipped with a mechanical stirrer, a thermometer, a cooler, a dropping funnel and an argon inlet was charged under argon in sequence with 118.2 g (250 mmol) of 5-[[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione, 98.3 g (375 mmol) of 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-, diethyl ester, 563 ml of mesitylene and 17.4 ml (125 mmol) of triethylamine. The suspension was stirred at reflux (ca. 167° C.) for 6 h, then the resulting solution was cooled to 90° C. within 50 min, finally 1560 ml of ethanol were added within 10 min whereas the temperature dropped to 40° C. The suspension was cooled to 0° C. and stirred at this temperature for 5 h. Finally the precipitate was isolated by filtration, the filter cake was washed with 700 ml of ethanol and dried over night at 60° C./10 mbar, to afford 101.1 g (92.3%) of 5-{[4-[2-(5-methyl-2-phenyl-oxazol-4-yl)ethoxy]benzo[b]thiophen-7-yl]methyl}-2,4-thiazolidinedione as off-white crystalline material with a m.p. of 208° C.

後処理

  1. customA 2.5 l, 4-necked glass flask equipped with a mechanical stirrer
  2. temperaturethe resulting solution was cooled to 90° C. within 50 min
  3. additiondropped to 40° C
  4. temperatureThe suspension was cooled to 0° C.
  5. stirringstirred at this temperature for 5 h
  6. customFinally the precipitate was isolated by filtration
  7. washthe filter cake was washed with 700 ml of ethanol
  8. customdried over night at 60° C./10 mbar

出典と根拠

ORDレコード
ord-fd0b7e36a61d46a0a4b7f0586cc07870
出典データセット
uspto-grants-2007_08
特許番号
US07259176B2

関連ノート

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