Triethylamine → 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamide

HRID 381383노트

반응식

HRID 381383 반응식
C(N(CC)CC)C.[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][N:27]=3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[CH2:47][CH2:48][NH2:49]>C(Cl)Cl>[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([NH:49][CH2:48][CH2:47][C:43]4[S:42][CH:46]=[CH:45][CH:44]=4)=[O:32])=[CH:28][N:27]=3)=[O:25])[CH2:22][CH2:23]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:9])[CH3:10]

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 62493Pivaloyl chlorideHCID 116521ThiopheneethanamineHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

생성물 1

HCID 183628556-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamide수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

Triethylamine (0. 8 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid (2g) in methylene chloride (30 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 for 1 hour. With the successive addition of triethylamine (0.9 ml) and 2-thiophenethylamine (0.75 g), the mixture was stirred at 5° C.˜10° C. for 2 hours. The solution was washed with an aqueous sodium bicarbonate and water. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid, so obtained, was recrystallized with ethanol and hexane to give a desired compound of 1.92 g (yield: 74%).

후처리

  1. temperaturecooled
  2. stirringthe mixture was stirred at 5° C.˜10° C. for 2 hours
  3. washThe solution was washed with an aqueous sodium bicarbonate and water
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated residue was treated with ether for crystallization
  7. customThe solid, so obtained
  8. customwas recrystallized with ethanol and hexane

출처 및 근거

ORD 기록
ord-4884cd17793d419096a507e3e8d4d7b5
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306860B1

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