5-(Isocyanatomethyl)-1,2,3-trimethoxybenzene → 4-Oxo-3-(3,4,5-trimethoxybenzyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098287노트

반응식

HRID 2098287 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH2:6][N:7]=[C:8]=[O:9].[N+:17](=[C:19]1[N:23]=[CH:22][N:21]=[C:20]1[C:24]([NH2:26])=[O:25])=[N-:18]>CS(C)=O>[O:9]=[C:8]1[N:7]([CH2:6][C:5]2[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=[N:17][C:19]2=[C:20]([C:24]([NH2:26])=[O:25])[N:21]=[CH:22][N:23]12

참가 물질

4

반응물 2

HCID 51886915-(Isocyanatomethyl)-1,2,3-trimethoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

생성물 1

HCID 441283774-Oxo-3-(3,4,5-trimethoxybenzyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

3,4,5-Trimethoxybenzyl isocyanate (Sigma Aldrich) (0.536 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product removed by filtration, washed with water and ethyl acetate, and then recrystallised from chloroform/hexane to give an off-white powder. Yield: 0.323 g, 45%. IR vmax/cm−1 1740, 1690, 1589. 1H NMR δH (DMSO-d6) 3.64 (3H, s, 4-OMe), 3.76 (6H, s, 3,5-OMe), 5.42 (2H, s, CH2Ar), 6.75 (2H, s, ArH), 7.68 (1H, br s, NH), 7.81 (1H, br s, NH), 8.84 (1H, s, 6-H). δC (DMSO-d6) 52.5, 56.4, 60.4, 105.9, 129.4, 131.3, 131.7, 134.9, 137.6, 139.7, 153.4, 162.0. MS Found 361.1300. Calc for (M+H): 361.1260. Found C, 49.5; H, 4.4; N, 23.2. Calc. for C15H16N6O5C, 50.0; H, 4.5; N, 23.3%.

후처리

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product removed by filtration
  3. washwashed with water and ethyl acetate
  4. customrecrystallised from chloroform/hexane
  5. customto give an off-white powder

출처 및 근거

ORD 기록
ord-bf4469c4dffc43ff9189729f3a14c4a7
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450479B2

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