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

HRID 1063794ノート

反応式

HRID 1063794 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-0f079f0bd6094d0bb0f1bdbc27d76792
出典データセット
uspto-grants-2005_11
特許番号
US06967204B2

反応ノート

読み込み中…