1H-Pyrazole-3-carboxamide, 5-(1-methylethyl)-4-nitro- → 4-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamide

HRID 1063794노트

반응식

HRID 1063794 반응식
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH2:11])=[O:10])[C:5]=1[N+:12]([O-])=O)([CH3:3])[CH3:2]>[Pd].C(O)C>[NH2:12][C:5]1[C:6]([C:9]([NH2:11])=[O:10])=[N:7][NH:8][C:4]=1[CH:1]([CH3:3])[CH3:2]

참가 물질

4

반응물 1

HCID 160997461H-Pyrazole-3-carboxamide, 5-(1-methylethyl)-4-nitro-

생성물 1

HCID 160997494-amino-3-(propan-2-yl)-1H-pyrazole-5-carboxamide수율 102.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

5-Isopropyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (3 g, 15.1 mmol) and 10% palladium on carbon (500 mg) in ethanol (30 ml) were stirred under hydrogen (50 psi) at room temperature for 18 hours. The reaction mixture was filtered and the solid was washed with methanol (50 ml), dichloromethane (50 ml), ethanol (50 ml) and ethyl acetate (50 ml). The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel eluting with dichloromethane methanol (9:1, by volume) to give 4-amino-5-isopropyl-1H-pyrazol-3-carboxylic acid amide (2.6 g) as an off-white solid. 1H NMR (400 MHz, DMSO-D6): δ=12.20-12.30 (1H, brs), 7.02-7.14 (1H, brs), 6.85-6.95 (1H, brs), 4.30-4.46 (2H, brs), 2.90-3.00 (1H, m), 1.15-1.21 (6H, d) ppm. LRMS (electrospray): m/z [M−H]+ 167, [2M−H]+ 335. Anal. Found C, 49.86; H, 7.21; N, 33.07. C7H12N4O requires C, 49.99; H, 7.19; N, 33.31%.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with methanol (50 ml), dichloromethane (50 ml), ethanol (50 ml) and ethyl acetate (50 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel eluting with dichloromethane methanol (9:1, by volume)

출처 및 근거

ORD 기록
ord-0f079f0bd6094d0bb0f1bdbc27d76792
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967204B2

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