Triethylamine → 4-(2-Ethoxybenzamido)-1-methyl-3-propylpyrazole-5-carboxamide

HRID 862896

反応式

HRID 862896 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])[CH3:2].[NH2:13][C:14]1[C:15]([CH2:23][CH2:24][CH3:25])=[N:16][N:17]([CH3:22])[C:18]=1[C:19]([NH2:21])=[O:20].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:13][C:14]1[C:15]([CH2:23][CH2:24][CH3:25])=[N:16][N:17]([CH3:22])[C:18]=1[C:19]([NH2:21])=[O:20])=[O:7])[CH3:2]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 30163972-Ethoxybenzoyl chlorideHCID 33380444-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 8501354-(2-Ethoxybenzamido)-1-methyl-3-propylpyrazole-5-carboxamide収率 40.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2-ethoxybenzoyl chloride (6.1 g, 33.0 mmol) in dichloromethane (50 ml) was added to a stirred solution of 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide (3.0 g, 16.4 mmol), 4-dimethylaminopyridine (0.02 g, 0.164 mmol) and triethylamine (3.34 g, 33.0 mmol) in dichloromethane (50 ml) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for a further 2 hours. The solvent was evaporated under vacuum, the residue dissolved in a 19:1 mixture of dichloromethane and methanol (250 ml), and then the solution washed with 1N hydrochloric acid (100 ml), dried (MgSO4) and evaporated under vacuum. The crude material was chromatographed on silica gel (200 g), eluting with a 97:3 mixture of dichlormethane and methanol, to give a pink solid; crystallisation from ethyl acetate-hexane gave the pyrazole-5-carboxamide as a pale pink solid (2.2 g, 40%), m.p. 153°-155° C. Found: C,61.66; H,6.77; N,16.95. C17 H22N4O3 requires C,61.80; H,6.71; N,16.96%.

後処理

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in a 19:1 mixture of dichloromethane and methanol (250 ml)
  3. washthe solution washed with 1N hydrochloric acid (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under vacuum
  6. customThe crude material was chromatographed on silica gel (200 g)
  7. washeluting with a 97:3 mixture of dichlormethane and methanol
  8. customto give a pink solid
  9. customcrystallisation from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-89b343d5237544aa98dde68edeee0539
出典データセット
uspto-grants-1998_02
特許番号
US05719283

関連ノート

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