HCID 19709759, 화합물 → HCID 58270459, 화합물

HRID 472154

반응식

HRID 472154 반응식
[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

참가 물질

5

반응물 2

HCID 19709759HCID 19709759, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 58270459HCID 58270459, 화합물수율 82%

시약·촉매·용매 2

HCID 934Nickel cation촉매HCID 21705897Ammonia methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-36d3c6d611b8452b9e71b29f7cdebd38
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633208B2

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