Water → 5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole

HRID 2182420ノート

反応式

HRID 2182420 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]([NH2:12])=[CH:8][C:9]=1[CH2:10][CH3:11])[CH3:2].[N+:14]([C:17]1[C:18]([CH:28]=O)=[N:19][N:20]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:21]=1)([O-:16])=[O:15].S(=O)(O)[O-].[Na+].O>CN(C)C=O>[CH2:1]([O:3][C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]2[NH:12][C:28]([C:18]3[C:17]([N+:14]([O-:16])=[O:15])=[CH:21][N:20]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][O:23]4)[N:19]=3)=[N:13][C:6]=2[CH:5]=1)[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 224777164-Ethoxy-5-ethyl-benzene-1,2-diamineHCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehydeHCID 23665763Sodium Bisulfite

生成物 1

HCID 1358046575-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-ethoxy-5-ethyl-benzene-1,2-diamine [0.18 g, Reference Example 30(s)], 4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carbaldehyde [0.225 g, Reference Example 6(m)] and sodium bisulfite (0.12 g, 1.2 mmol) in dimethylformamide (10 mL) was heated at 120° C. for 1 hour. The mixture was cooled, water (100 mL) was added and the aqueous mixture was extracted with twice ethyl acetate (50 mL). The combined extracts were evaporated and the residue was chromatographed on silica gel (ethyl acetate with gradient of 20-0% heptane) to give 5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole (200 mg) as a solid. LC-MS (Method E) RT=2.85 minutes, 386 (M+H)+. (b) 2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1,5,6,7-tetrahydro-1,3-diaza-s-indacene

後処理

  1. temperatureThe mixture was cooled
  2. extractionthe aqueous mixture was extracted with twice ethyl acetate (50 mL)
  3. customThe combined extracts were evaporated
  4. customthe residue was chromatographed on silica gel (ethyl acetate with gradient of 20-0% heptane)

出典と根拠

ORDレコード
ord-527252f2c25545fc9f466cafe4a1e05f
出典データセット
uspto-grants-2005_05
特許番号
US06897208B2

反応ノート

読み込み中…