1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

HRID 534876노트

반응식

HRID 534876 반응식
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH:19]([C:21]1[C:22]([CH3:32])=[N:23][N:24]([CH3:31])[C:25]=1[S:26][CH2:27][C:28](O)=[O:29])=[O:20].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O.C(N(CC)CC)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:28](=[O:29])[CH2:27][S:26][C:25]2[N:24]([CH3:31])[N:23]=[C:22]([CH3:32])[C:21]=2[CH:19]=[O:20])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 470023932-[(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

생성물 1

HCID 866633985-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g), [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acid obtained in Reference Example 3 (736 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (786 mg), 1-hydroxy-1H-benzotriazole monohydrate (628 mg), triethylamine (1.39 mL), and N,N-dimethylformamide (50 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 80:20-30:70 hexane/ethyl acetate) to provide 5-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (900 mg, 64%) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel, 80:20-30:70 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-336bfa2e363c4b49b742b8062c47e5a5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853215B2

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