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

HRID 560795노트

반응식

HRID 560795 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-79e19b10ad364722be62e203bdd8982b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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