HCID 19709759、化合物 → HCID 58270459、化合物

HRID 472154

反応式

HRID 472154 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([C:14]#[N:15])[CH:8]=2)[CH:6]=1.[H][H]>N.CO.[Ni+2]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH2:14][NH2:15])[CH:8]=2)[CH:6]=1

参加物

5

反応物 2

HCID 19709759HCID 19709759、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 58270459HCID 58270459、化合物収率 82%

試薬・触媒・溶媒 2

HCID 934Nickel cation触媒HCID 21705897Ammonia methanol溶媒

実験手順

To 4-(4-methyl-1H-imidazol-1-yl)-2-cyanoaniline (15.5 g; 78.2 mmol) dissolved in 10% NH3/methanol was added Raney-Nichel (5 g), the resulting mixture was hydrogenated at 60° C., at an hydrogen pressure of 60 bar, for 24 hours. The nitrogen purged reaction mixture was filtered on celite, the cake was washed with methanol and the combined filtrate and washings evaporated. The residue was purified by column chromatography over silica gel (DCM/MeOH/2M NH3, 85:10:5) evaporation of the combined appropriate fractions afforded the pure titled product as yellow-orange solid (12.9 g, 82%). C11H14N4, MW: 202.26; 1H-NMR (300 MHz, d6-DMSO) ppm: 2.13 (s, 3H), 5.24 (s, 2H), 6.67 (d, 1H), 7.08 (dd, 1H), 7.17 (t, 1H), 7.23 (d, 1H), 7.81 (d, 1H).

後処理

  1. customThe nitrogen purged
  2. customreaction mixture
  3. filtrationwas filtered on celite
  4. washthe cake was washed with methanol
  5. customthe combined filtrate and washings evaporated
  6. customThe residue was purified by column chromatography over silica gel (DCM/MeOH/2M NH3, 85:10:5) evaporation of the combined appropriate fractions

出典と根拠

ORDレコード
ord-36d3c6d611b8452b9e71b29f7cdebd38
出典データセット
uspto-grants-2014_01
特許番号
US08633208B2

関連ノート

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