Hydrochloric Acid → 1-Benzyl-6-chloro-2-{1-[3-(1-isopropyltetrazol-5-yl)propyl]indol-5-ylaminocarbonyl}benzimidazole

HRID 609765

反応式

HRID 609765 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][C:14]1[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[N:16][N:15]=1)[CH:6]=[CH:5]2.C[Al](C)C.[CH2:26]([N:33]1[C:37]2[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1[C:43](OC)=[O:44])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CO.ClCCl.CCCCCC.C1(C)C=CC=CC=1>[CH2:26]([N:33]1[C:37]2[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1[C:43]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][C:14]1[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[N:16][N:15]=1)[CH:6]=[CH:5]2)=[O:44])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 16682925TrimethylaluminumHCID 196004025-Amino-1-[3-(1-isopropyl-5-tetrazolyl)propyl]indoleHCID 19600410Methyl 1-benzyl-6-chlorobenzimidazol-2-carboxylate

生成物 1

HCID 196003911-Benzyl-6-chloro-2-{1-[3-(1-isopropyltetrazol-5-yl)propyl]indol-5-ylaminocarbonyl}benzimidazole

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To 2.2 g of 5-amino-1-[3-(1-isopropyl-5-tetrazolyl)propyl]indole was added 40 ml of toluene, then this mixture was stirred under nitrogen gas atmosphere by cooling in a methanol-ice bath. To this reaction mixture was added 4 ml of n-hexane solution of 2M trimethylaluminum dropwise from syringe, then reaction mixture was stirred for 20 minutes, and further stirred at room temperature for 1 hour. 2.18 Grams of methyl 1-benzyl-6-chlorobenzimidazol-2-carboxylate was added to the reaction mixture and was stirred for 5 to 6 hours under refluxing condition. Next, 10% hydrochloric acid was added, and the crystals being separated were collected by filtration. Water-chloroform was added to the crystals, this solution was made alkaline with 10% aqueous solution of potassium hydroxide, then was filtered with Celite, the chloroform layer was washed with water, an aqueous solution saturated with sodium chloride. The chloroform layer was dried with anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: 3% methanol/dichloromethane), and recrystallized from ethyl acetate-n-hexane, there was obtained 2.27 g of 1-benzyl-6-chloro-2-{1-[3-(1-isopropyltetrazol-5-yl)propyl]indol-5-ylaminocarbonyl}benzimidazole as in the form of yellow needle crystals.

後処理

  1. temperatureby cooling in a methanol-ice bath
  2. customreaction mixture
  3. stirringwas stirred for 20 minutes
  4. stirringfurther stirred at room temperature for 1 hour
  5. stirringwas stirred for 5 to 6 hours
  6. temperatureunder refluxing condition
  7. customthe crystals being separated
  8. filtrationwere collected by filtration
  9. additionWater-chloroform was added to the crystals
  10. filtrationwas filtered with Celite
  11. washthe chloroform layer was washed with water
  12. dry with materialThe chloroform layer was dried with anhydrous magnesium sulfate
  13. customthe solvent was removed under reduced pressure
  14. customThe residue thus obtained
  15. customrecrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-aaecb0356e914ede9d44df8a269e4c2e
出典データセット
uspto-grants-1999_12
特許番号
US05998437

関連ノート

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