Nicotinic Acid → HCID 19600415、化合物

HRID 609769ノート

反応式

HRID 609769 の反応式
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10]([N:17]1[C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[C:27]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH2:39][CH2:40][CH2:41][NH2:42])[CH:34]=[CH:33]2)=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(OP(C#N)(=O)OCC)C>CN(C)C=O.O>[CH2:10]([N:17]1[C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[C:27]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH2:39][CH2:40][CH2:41][NH:42][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])[CH:34]=[CH:33]2)=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 19600385HCID 19600385、化合物

生成物 1

HCID 19600415HCID 19600415、化合物収率 75.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To 0.29 g of nicotinic acid was added 50 ml of dimethylformamide, further 1.2 g of 1-benzyl-6-chloro-2-[1-(3-aminopropyl)indol-5-ylaminocarbonyl]-benzimidazole and 0.7 ml of triethylamine were added, the mixture was stirred under cooling at 0° C. Next, 0.49 g of diethylcyanophosphonate was dissolved in 20 ml of dimethylformamide and added thereto and the reaction mixture was stirred at room temperature for 1 day. After the reaction was finished, water was added then the whole mixture was extracted with ethyl acetate, the extract thus obtained was washed with water and an aqueous solution saturated with sodium chloride. The washed extract was dried with anhydrous magnesium sulfate, then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (eluent: 2% methanol/dichloromethane), recrystallized from chloroform, there was obtained 1 g of 1-benzyl-6-chloro-2-{1-[3-(pyridin-3-ylcarbonylamino)propyl]indol-5-ylaminocarbonyl}benzimidazole as in the form of yellow needle crystals.

後処理

  1. additionwere added
  2. additionadded
  3. stirringthe reaction mixture was stirred at room temperature for 1 day
  4. extractionthe whole mixture was extracted with ethyl acetate
  5. extractionthe extract thus
  6. customobtained
  7. washwas washed with water
  8. extractionThe washed extract
  9. dry with materialwas dried with anhydrous magnesium sulfate
  10. customthe solvent was removed by distillation under reduced pressure
  11. customrecrystallized from chloroform

出典と根拠

ORDレコード
ord-9e19dc40df064cbabf38fdc428f15528
出典データセット
uspto-grants-1999_12
特許番号
US05998437

反応ノート

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