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

HRID 975885ノート

反応式

HRID 975885 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-444175e1d4fc486bb8c379163b1a993d
出典データセット
uspto-grants-1997_03
特許番号
US05610156

反応ノート

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