Diisopropylethylamine → Methyl 6-[[bis(2-biphenylcarbonyl)]amino]pyridine-3-carboxylate

HRID 1735225노트

반응식

HRID 1735225 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(N([CH:18]([CH3:20])[CH3:19])CC)(C)C.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22]([C:27](Cl)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>ClCCl.O>[C:23]1([C:19]2[CH:18]=[CH:20][CH:35]=[CH:30][CH:31]=2)[C:22]([C:27]([N:1]([C:27]([C:22]2[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:28])[C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=2)=[O:28])=[CH:21][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 737487Methyl 6-aminonicotinateHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

생성물 1

HCID 22099573Methyl 6-[[bis(2-biphenylcarbonyl)]amino]pyridine-3-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

To a chilled (0° C.) solution of 2.64 g of methyl 6-aminopyridine-3-carboxylate and 5.5 ml of diisopropylethylamine in 30 ml of dichloromethane under argon is added 6.8 g of 2-biphenylcarbonyl chloride in 10 ml of dichloromethane. The mixture is stirred at room temperature 2 days and then diluted with 120 ml of dichloromethane and 50 ml of water. The organic layer is separated, washed with 50 ml each of 1M NaHCO3 and brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated under vacuum to give a solid. Crystallization from ethyl acetate gives 6.2 g of white crystals, m.p. 180°-188° C.

후처리

  1. customThe organic layer is separated
  2. washwashed with 50 ml each of 1M NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated under vacuum
  6. customto give a solid
  7. customCrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-d95a46d8449a4f41919af8ad6ece98a6
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05536718

반응 노트

불러오는 중…