Triethylamine → 5-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide

HRID 57795

반응식

HRID 57795 반응식
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH2:38])=[CH:32][CH:31]=1.CCN=C=NCCCN(C)C>O1CCCC1.O>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH:38][C:9]([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=2)=[O:11])=[CH:32][CH:31]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 674302-(4-Chlorophenyl)ethylamineHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 1363443545-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-nitro-1H-pyrazole-3-carboxylic acid (200 mg, 1.3 mmol, 1 eq) in tetrahydrofuran (5 mL) were added triethylamine (350 μL, 1.9 mmol, 1.5 eq), hydroxybenzotriazole (HOBT) (257 mg, 1.27 mmol, 1 eq), 2-(4-chloro-phenyl)-ethylamine (180 μL, 1.27 mmol, 1 eq) and EDCI (364 mg, 1.9 mmol, 1.5 eq). The mixture was stirred at room temperature during 20 h. Water (10 mL) was then added and the aqueous phase was extracted with ethyl acetate (2×15 mL). The organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (100/0) to (50/50) to afford 5-nitro-1H-pyrazole-3-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-amide as white solid (160 mg, 43% yield).

후처리

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×15 mL)
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-7a0f096c90634fb5b970bdaed8626bd8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434745B2

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