Triethylamine → 3-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazide

HRID 78585

반응식

HRID 78585 반응식
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[NH2:30][C:31]1[C:32]([C:38]([OH:40])=O)=[N:33][C:34]([Br:37])=[CH:35][N:36]=1.[C:41]([NH:49][NH2:50])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C.O>[NH2:30][C:31]1[C:32]([C:38]([NH:50][NH:49][C:41]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:48])=[O:40])=[N:33][C:34]([Br:37])=[CH:35][N:36]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

생성물 1

HCID 594723553-amino-6-bromo-N'-(phenylcarbonyl)pyrazine-2-carbohydrazide수율 73.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

TBTU (22.09 g, 68.80 mmol) and triethylamine (4.642 g, 6.394 mL, 45.87 mmol) were added to a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol) and benzohydrazide (7.494 g, 55.04 mmol) in DMF (100.0 mL) and the resulting solution stirred at ambient temperature for 48 hours and then poured into water (400 mL) with vigorous stirring. This was allowed to stir for 30 minutes, filtered and washed with water. The moist solid was dissolved in hot EtOAc, dried (MgSO4), filtered and concentrated in vacuo and the resultant solid dried under vacuum to give the desired product (11.34 g, 73% Yield). 1H NMR (400.0 MHz, DMSO) d 7.51 (2H, m), 7.61 (1H, m), 7.69 (2H, br s), 7.92 (2H, m), 8.44 (1H, s), 10.48 (1H, br s), 10.54 (1H, br s) ppm; MS (ES+) 338.01

후처리

  1. stirringto stir for 30 minutes
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe moist solid was dissolved in hot EtOAc
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resultant solid dried under vacuum

출처 및 근거

ORD 기록
ord-cd25e745e6ad4c6c8a4d53b81cbc2ae8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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