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

HRID 381383ノート

反応式

HRID 381383 の反応式
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]

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 62493Pivaloyl chlorideHCID 116521ThiopheneethanamineHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4884cd17793d419096a507e3e8d4d7b5
出典データセット
uspto-grants-2001_10
特許番号
US06306860B1

反応ノート

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