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

HRID 78585

反応式

HRID 78585 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-cd25e745e6ad4c6c8a4d53b81cbc2ae8
出典データセット
uspto-grants-2014_09
特許番号
US08841308B2

関連ノート

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