Triethylamine → 4-[(5-acetyl-2-propoxybenzoyl)amino]-5-ethyl-1H-pyrazole-3-carboxamide

HRID 1837553ノート

反応式

HRID 1837553 の反応式
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH3:22])=[C:14]([CH:18]=1)[C:15]([OH:17])=O)(=[O:9])[CH3:8].C(N(CC)CC)C.[NH2:30][C:31]1[C:32]([CH2:39][CH3:40])=[N:33][NH:34][C:35]=1[C:36]([NH2:38])=[O:37]>CN(C)C=O.ClCCl>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH3:22])=[C:14]([CH:18]=1)[C:15]([NH:30][C:31]1[C:35]([C:36]([NH2:38])=[O:37])=[N:34][NH:33][C:32]=1[CH2:39][CH3:40])=[O:17])(=[O:9])[CH3:8]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 226781155-Acetyl-2-n-propoxybenzoic acidHCID 178438044HCID 178438044、化合物

生成物 1

HCID 226781184-[(5-acetyl-2-propoxybenzoyl)amino]-5-ethyl-1H-pyrazole-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (5.45 ml, 46.4 mmol) was added to a solution of 5-acetyl-2-n-propoxy-benzoic acid (WO 9312095) (11.1 g, 30.9 mmol) in N,N-dimethylformamide (0.1 ml) and dichloromethane (200 ml) under nitrogen at room temperature. Once addition was complete the solution was stirred for 1 hour. The solution was concentrated under reduced pressure and azeotroped with toluene, and the intermediate acid chloride was dissolved in dichloromethane (200 ml). Triethylamine (10.4 ml, 46.4 mmol) was added followed by 4-amino-3-ethyl-1H-pyrazole-5-Carboxamide (WO 9849166) (7.7 g, 30.9 mmol) and the reaction was stirred at room temperature for 16 hours. The mixture was washed with 1N hydrochloric acid (2×100 ml), 10% sodium bicarbonate solution (100 ml) and brine (100 ml), dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was recrystallised from acetonitrile to afford the title compound as a crystalline solid, 14.8 g.

後処理

  1. additionOnce addition
  2. concentrationThe solution was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. dissolutionthe intermediate acid chloride was dissolved in dichloromethane (200 ml)
  5. stirringthe reaction was stirred at room temperature for 16 hours
  6. washThe mixture was washed with 1N hydrochloric acid (2×100 ml), 10% sodium bicarbonate solution (100 ml) and brine (100 ml)
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was recrystallised from acetonitrile

出典と根拠

ORDレコード
ord-09c46aa1fd624eedafd9eb5d9297d030
出典データセット
uspto-grants-2004_08
特許番号
US06784185B2

反応ノート

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