Hydrochloric Acid → ethyl 5-amino-3-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate

HRID 1748429ノート

反応式

HRID 1748429 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH2:10])=[N:7][CH:8]=1.[C:13]([C:15](=[C:21](OCC)[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].C(O)C.Cl>O>[NH2:14][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:8][N:7]=2)[N:10]=[C:21]([CH3:22])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 14776422-Hydrazinyl-5-(trifluoromethyl)pyridine

生成物 1

HCID 86692405ethyl 5-amino-3-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate収率 54.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5-(Trifluoromethyl)pyridin-2-ylhydrazine (10.0 g) described in Reference Example 8 and ethyl 2-cyano-3-ethoxy-3-methylacrylate (10.3 g) were added to a mixed solvent of ethanol (40 ml) and 1N hydrochloric acid aqueous solution (40 ml), and the mixture was stirred at reflux temperature for three hours. Water was added to the reaction solution to give ethyl 5-amino-3-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate (9.6 g). Next, the compound was added to tetrahydrofuran (50 ml), isoamyl nitrite (20 g) was added and the mixture was stirred at reflux temperature for five hours. The reaction solution was concentrated, a mixed solvent of ethanol (40 ml) and water (40 ml) and sodium hydroxide (5 g) were added and the mixture was stirred at reflux temperature for two hours. Ethanol was evaporated, diluted hydrochloric acid was added and the precipitated solid was recrystallized from aqueous methanol to give the titled compound.

後処理

  1. temperatureat reflux temperature for three hours

出典と根拠

ORDレコード
ord-f5c504daa7a645d79df7569f884a840a
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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