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 2098287ノート

反応式

HRID 2098287 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-bf4469c4dffc43ff9189729f3a14c4a7
出典データセット
uspto-grants-2013_05
特許番号
US08450479B2

反応ノート

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