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Isopropanol → 2-(2-Methylpyrazolo[1,5-a]pyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole-5-carboxylic acid

HRID 2282223
ノート
印刷プレビュー

反応式

HRID 2282223 の反応式
Cl.[CH3:2][C:3]1[C:11]([C:12](=[S:14])[NH2:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.Cl[CH:16]([C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])=O)[C:17]([O:19]CC)=[O:18].CC(O)C.C(=O)(O)[O-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:2][C:3]1[C:11]([C:12]2[S:14][C:16]([C:17]([OH:19])=[O:18])=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])[N:13]=2)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochlorideHCID 86649598Ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoate

生成物 1

HCID 668550542-(2-Methylpyrazolo[1,5-a]pyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole-5-carboxylic acid収率 31.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (1.2 g, 5.2 mmol) obtained in Example 11-B(v), ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoate (1.7 g, 8.4 mmol) obtained above and 2-propanol (20 mL) was stirred at 80° C. for 4 h. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate, EtOAc and THF. Insoluble materials were removed by filtration and the filtrate was extracted with a 1:1 mixture of EtOAc and THF. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. To the residue were added MeOH (10 mL), THF (25 mL) and 8N aqueous sodium hydroxide solution (2.5 mL), and the mixture was stirred at 70° C. for 1 h. The reaction mixture was allowed to cool to 0° C., 6N hydrochloric acid was added to adjust the solution to about pH 3.0. The resulting precipitate was collected by filtration, washed with diisopropyl ether, and dried to give the title compound (620 mg, 31%) as a yellow solid.

後処理

  1. customInsoluble materials were removed by filtration
  2. extractionthe filtrate was extracted with a 1:1 mixture of EtOAc and THF
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customInsoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionTo the residue were added MeOH (10 mL), THF (25 mL) and 8N aqueous sodium hydroxide solution (2.5 mL)
  8. stirringthe mixture was stirred at 70° C. for 1 h
  9. temperatureto cool to 0° C.
  10. addition6N hydrochloric acid was added
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with diisopropyl ether
  13. customdried

出典と根拠

ORDレコード
ord-d6359840dd624074860fc7bfc0e6db0f
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139589B2

反応ノート

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