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

HRID 1532108

반응식

HRID 1532108 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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 dichloromethane and methanol, to give a pink solid; crystallisation from ethyl acetate-hexane gave the pyrazole-3-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. C17H22N4O3 requires C,61.80; H,6.71; N,16.96%.

후처리

  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 dichloromethane and methanol
  8. customto give a pink solid
  9. customcrystallisation from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-8bf503ef27334a319be12e62bc32be4e
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200980B1

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