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

HRID 1896203

반응식

HRID 1896203 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b28515ed3cb94be1a17cff64f6fdab36
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518956B2

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