1,2-Diaminocyclohexane → N-benzyl-2-(3-benzyl-2-(cyanoimino)imidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 560795ノート

反応式

HRID 560795 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14](Br)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][NH:27][C:26]1=[N:30][C:31]#[N:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(N)CCCCC1N.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:27]2[CH2:28][CH2:29][N:25]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:26]2=[N:30][C:31]#[N:32])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 46101,2-DiaminocyclohexaneHCID 11430Potassium CarbonateHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178512076HCID 178512076、化合物

生成物 1

HCID 59481237N-benzyl-2-(3-benzyl-2-(cyanoimino)imidazolidin-1-yl)-4-methylthiazole-5-carboxamide収率 8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (0.25 g, 0.80 mmol). N-(1-benzylimidazolidin-2-ylidene)cyanamide (0.18 g, 0.88 mmol), copper(I) iodide (0.030 g, 0.16 mmol), cyclohexane-1,2-diamine (0.018 g, 0.16 mmol) and potassium carbonate (0.17 g, 1.20 mmol) in anhydrous N,N-dimethylformamide (15 mL) was heated at 100° C. under nitrogen atmosphere for 16 hours. The solvent was removed in vacuo diluted with ethyl acetate (250 mL), washed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexane to afford the title compound as a colourless solid in 8% yield (0.030 g): mp 226-228° C. (ethyl acetate/hexanes): 1H NMR (300 MHz, DMSO-d6) δ 8.59 (t, J=5.9 Hz, 1H), 7.49-7.17 (m, 10H), 4.99 (s, 2H), 4.35 (d, J=5.9 Hz, 2H), 4.14-4.08 (m, 2H), 3.66-3.60 (m, 2H), 2.44 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.9, 156.1, 153.3, 151.5, 140.0, 135.4, 129.3, 128.7, 128.4, 128.1, 127.7, 127.1, 119.8, 113.9, 49.0, 46.6, 44.72, 43.1, 17.5; MS (ES+) m/z 431.3 (M+1).

後処理

  1. customThe solvent was removed in vacuo
  2. additiondiluted with ethyl acetate (250 mL)
  3. washwashed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ethyl acetate and hexane
  8. filtrationThe solid was collected by filtration
  9. washwashed with methanol and hexane

出典と根拠

ORDレコード
ord-79e19b10ad364722be62e203bdd8982b
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

反応ノート

読み込み中…