Ammonium formate → 4-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide

HRID 1896203

反応式

HRID 1896203 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]([NH2:13])=[O:12])=[C:9]([N+:14]([O-])=O)[C:8]([CH2:17][CH3:18])=[N:7]1)[CH3:2].C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:14][C:9]1[C:8]([CH2:17][CH3:18])=[N:7][N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:10]=1[C:11]([NH2:13])=[O:12]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 577445561-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide

生成物 1

HCID 577445394-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide収率 49.2%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

A mixture of 1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide from step 1 (5.70 g, 22 mmol) and palladium hydroxide (1.0 g) in ethanol (110 mL) was treated with ammonium formate (7.01 g, 111 mmol) in four unequal portions at about 10 minute intervals. The resulting mixture was heated under reflux for two hours and then cooled. The mixture was filtered through celite and concentrated. The resulting residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane as the eluent to provide 2.45 g of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.17 (t, 3 H), 1.21-1.32 (m, 3 H), 2.60 (q, 2 H), 3.53 (q, 2 H), 3.79-3.95 (m, 2 H), 4.38-4.52 (m, 2 H). MS (ESI) m/z 227.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for two hours
  3. temperaturecooled
  4. filtrationThe mixture was filtered through celite and
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography on silica gel using
  7. additiona mixture of ethyl acetate and hexane as the eluent

出典と根拠

ORDレコード
ord-b28515ed3cb94be1a17cff64f6fdab36
出典データセット
uspto-grants-2013_08
特許番号
US08518956B2

関連ノート

読み込み中…