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Benzoic Acid → n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}benzamide

HRID 353077
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인쇄 미리보기

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HRID 353077 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]=1[CH2:11][CH3:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 243Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

생성물 1

HCID 10181088n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}benzamide수율 37.2%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 6228Dimethylformamide용매

실험 절차

A solution of the amine of Example 43 (98 mg, 0.30 mmol) in dimethylformamide (3.75 ml) was treated with benzoic acid (41 mg, 0.33 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (64 mg, 0.33 mmol) and 4-dimethylaminopyridine (81 mg, 0.66 mmol) and stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic extract was dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (48 mg) as a white solid, m.p. 115-117° C.

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

출처 및 근거

ORD 기록
ord-9c9cccd0de9e4accb3c839bf7c39bf80
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06750230B2

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