Phenylhydrazine → 3-amino-N-methyl-6-{3-[(2-phenylhydrazino)carbonyl]phenyl}pyrazine-2-carboxamide

HRID 646685노트

반응식

HRID 646685 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].O[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2N=[N:23]1.CN1CCOCC1.C1(NN)C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][C:5]([C:12]2[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([NH:23][NH:22][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=3)=[O:17])[CH:13]=2)=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 7516PhenylhydrazineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 587105713-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoic acid

생성물 1

HCID 686516823-amino-N-methyl-6-{3-[(2-phenylhydrazino)carbonyl]phenyl}pyrazine-2-carboxamide수율 56%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoic acid (40 mg, 0.15 mmol) was dissolved in DMF (1 mL) and 1-hydroxybenzotriazole (30 mg, 0.22 mmol), 1-[(3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (30 mg, 0.16 mmol), and 4-methylmorpholine (30 mg, 0.28 mol) were added sequentially. After one hour phenylhydrazine (30 mg, 0.27 mmol) was added to the reaction mixture and stirring was continued at room temperature for 18 hours. It was then diluted with ethyl acetate (10 mL), washed with water, saturated sodium bicarbonate solution, and brine, dried over sodium sulfate, filtered, and concentrated. The oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield) to give 3-amino-N-methyl-6-{3-[(2-phenylhydrazino)carbonyl]phenyl}pyrazine-2-carboxamide (a tan color solid, 30 mg, 56% yield): 1H NMR (400 MHz, DMSO-d6): 10.42 (b, 1H), 8.92 (s, 1H), 8.84-8.82 (b, 1H), 8.57-8.57 (s,1H0, 8.41-8.39 (d, 1H), 7.94-7.89(m, 1H), 7.89-7.86 (d, 1H), 7.61-7.57 (t, 1H), 7.17-7.13 (t, 1H), 6.83-6.80 (d, 1H), 6.73-6.69(m, 1H), 2.85 (s, 3H); MS (EI) for C19H18N6O2: 440 (MH+).

후처리

  1. washwashed with water, saturated sodium bicarbonate solution, and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield)

출처 및 근거

ORD 기록
ord-5356ade4271a43d1aab47896aa2b5376
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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