Nicotinic Acid → HCID 19600415, 화합물

HRID 609769노트

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HRID 609769 반응식
[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

참가 물질

7

반응물 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 19600385HCID 19600385, 화합물

생성물 1

HCID 19600415HCID 19600415, 화합물수율 75.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e19dc40df064cbabf38fdc428f15528
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998437

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