HCID 23402490, 화합물 → 4-amino-3-cyclopentyl-1H-pyrazole-5-carboxamide

HRID 1063813노트

반응식

HRID 1063813 반응식
[CH:1]1([C:6]2[NH:10][N:9]=[C:8]([C:11]([NH2:13])=[O:12])[C:7]=2[N+:14]([O-])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[NH2:14][C:7]1[C:8]([C:11]([NH2:13])=[O:12])=[N:9][NH:10][C:6]=1[CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 1

HCID 23402490HCID 23402490, 화합물

생성물 1

HCID 234024844-amino-3-cyclopentyl-1H-pyrazole-5-carboxamide수율 103%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

5-cyclopentyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (4.48 g, 20 mmol) and 10% palladium on carbon (800 mg) in ethanol (50 ml) were stirred under hydrogen (50 psi) at room temperature for 18 hours. The reaction mixture was filtered through arbocel and the solid was washed with ethanol (50 ml), methanol (50 ml), dichloromethane (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-cyclopentyl-1H-pyrazol-3-carboxylic acid amide (4.0 g) as an off-white solid which was a mixture of rotamers. 1H NMR (400 MHz, DMSO-D6): δ=12.20-12.31 (0.75H, brs), 11.78-11.87 (0.25H, brs), 7.02-7.18 (1.5H, brs), 6.80-6.93 (0.5H, brs), 4.22-4.56 (2H, 2×brs), 2.92-3.02 (1.96 (2H, m), 1.48-1.78 (6H, 2×m) ppm. LRMS (electrospray): m/z [M−H]+ 193. Anal. Found C, 56.12; H, 7.39; N, 27.55. C9H14N4O. 0.2 mol acetone requires C, 56.01; H, 7.44; N, 27.22%.

후처리

  1. filtrationThe reaction mixture was filtered through arbocel
  2. washthe solid was washed with ethanol (50 ml), methanol (50 ml), dichloromethane (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-627fe34d89f34a0e95d28b5f2704e505
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967204B2

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