Hydrochloric Acid → 5-(3-Phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazole

HRID 1585220ノート

反応式

HRID 1585220 の反応式
Cl.[N:2]1[C:6]2[CH2:7][CH2:8][CH:9]([C:11]([OH:13])=O)[CH2:10][C:5]=2[NH:4][CH:3]=1.[C:14]1([CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:14]1([CH:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([C:11]([CH:9]3[CH2:8][CH2:7][C:6]4[N:2]=[CH:3][NH:4][C:5]=4[CH2:10]3)=[O:13])[CH2:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 109323533-phenyl-2,3-dihydro-1H-indoleHCID 110301834,5,6,7-Tetrahydro-1H-benzoimidazole-5-carboxylic acid

生成物 1

HCID 98410295-(3-Phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazole収率 82.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixed solution of 518 mg of hydrochloride (racemic form) of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid, 500mg of (+)-3-phenylindoline, and 15 ml of dimethyl formamide was cooled to 0° C. The cooled solution and 736 mg of hydrochloride of N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide added thereto were gradually heated to normal room temperature and stirred at the same temperature for 12 hours. The resultant reaction solution was concentrated under a reduced pressure. The residue of this concentration was neutralized by addition of an aqueous potassium carbonate solution and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and then distilled. The residue of this distillation was refined by silica gel column chromatography to obtain 725 mg of 5-(3-phenylindolin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzimidazole (82.5%) as an epimer mixture.

後処理

  1. customThe resultant reaction solution
  2. concentrationwas concentrated under a reduced pressure
  3. concentrationThe residue of this concentration
  4. additionwas neutralized by addition of an aqueous potassium carbonate solution
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. distillationThe residue of this distillation

出典と根拠

ORDレコード
ord-3cae8705a75a425c82f7c09c94afe287
出典データセット
uspto-grants-1999_08
特許番号
US05936098

反応ノート

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