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Isopropylamine → 5-(n-Isopropylcarbamoyl)-2-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]pyridine

HRID 381365
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HRID 381365 반응식
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=3)=[O:17])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(Cl)(=O)C(C)(C)C.[CH:34]([N:37](CC)C(C)C)([CH3:36])[CH3:35].C(N)(C)C>C(Cl)Cl.C(N(CC)CC)C>[CH:34]([NH:37][C:22]([C:21]1[CH:25]=[CH:26][C:18]([C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=3)[CH2:15][CH2:14]2)=[O:17])=[N:19][CH:20]=1)=[O:24])([CH3:36])[CH3:35]
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참가 물질

7

반응물 4

HCID 6363IsopropylamineHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 183628396-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid

생성물 1

HCID 183628135-(n-Isopropylcarbamoyl)-2-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]pyridine수율 78%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8471Triethylamine용매

실험 절차

Triethylamine (0.85 ml) was added to 6-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid (2 g) in methylene chloride (25 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (0.7 ml) at 0° C.˜5° C., the mixture was stirred at 5° C.˜10° C. for 2 hours. With the addition of N,N-diisopropylethylamine (1.1 ml) and isopropylamine (0.55 ml), the mixture was stirred at 10° C.˜15° C. for 3 hours. The reaction mixture was washed with an aqueous sodium bicarbonate and water twice. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in chloroform (15 ml) and with the slow addition of ether, crystals were precipitated. For 2-hours stirring, the precipitate was filtered, washed (ether) and dried to give a desired compound of 1.74 g (yield: 78%).

후처리

  1. temperaturecooled
  2. stirringthe mixture was stirred at 10° C.˜15° C. for 3 hours
  3. washThe reaction mixture was washed with an aqueous sodium bicarbonate and water twice
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in chloroform (15 ml) and with the slow addition of ether, crystals
  7. customwere precipitated
  8. stirringFor 2-hours stirring
  9. filtrationthe precipitate was filtered
  10. washwashed (ether)
  11. customdried

출처 및 근거

ORD 기록
ord-cb25f6fce5564821a8203a3b17e8b609
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06306860B1

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