HCID 23402490、化合物 → 4-amino-3-cyclopentyl-1H-pyrazole-5-carboxamide

HRID 1063813ノート

反応式

HRID 1063813 の反応式
[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

参加物

4

反応物 1

HCID 23402490HCID 23402490、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-627fe34d89f34a0e95d28b5f2704e505
出典データセット
uspto-grants-2005_11
特許番号
US06967204B2

反応ノート

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