Sodium ethoxide → 6-Cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

HRID 2374406ノート

反応式

HRID 2374406 の反応式
CO[C:3]([C:5]1[N:6]([N:12]([C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:7]=[C:8]([C:10]#[N:11])[CH:9]=1)=[O:4].[O-]CC.[Na+]>C(O)C>[CH2:23]([O:22][C:20]([C:19]1[C:18](=[O:25])[N:12]([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[N:6]2[CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:5]2[C:3]=1[OH:4])=[O:21])[CH3:24]

参加物

4

反応物 2

HCID 2723922Sodium ethoxideHCID 687765484-cyano-1-[(2-ethoxycarbonyl-acetyl)-(3-methyl-butyl)-amino]-1H-pyrrole-2-carboxylic acid methyl ester

生成物 1

HCID 598535636-Cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
40 °C

実験手順

To a solution of crude 4-cyano-1-[(2-ethoxycarbonyl-acetyl)-(3-methyl-butyl)-amino]-1H-pyrrole-2-carboxylic acid methyl ester (Example 15d, 2.552 mmol) in ethanol (30 mL) was added a 21% solution of sodium ethoxide in ethanol (2.07 g, 6.380 mmol) and the mixture was heated at 40° C. for 16 h. Upon cooling, the mixture was quenched with 1.0 M aqueous hydrochloric acid solution and brine. The aqueous mixture was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude desired product, 6-cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester as a yellow solid, which was used in the next step without further purification. LC-MS (ESI) calcd for C16H19N3O4 317.14. found 318.3 [M+H+]. FT-IR (ATR) νmax (neat): 2231, 1642, 1610 cm−1.

後処理

  1. temperatureUpon cooling
  2. customthe mixture was quenched with 1.0 M aqueous hydrochloric acid solution and brine
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-359a06b34b3f4e9e8fc8ebd19422c702
出典データセット
uspto-grants-2008_12
特許番号
US07462611B2

反応ノート

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