Triethylamine → ethyl 2-[[(2R)-2-[1-methyl-2-[[4-[N-(4-methylbenzoyl)carbamimidoyl]anilino]methyl]benzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

HRID 1357801ノート

反応式

HRID 1357801 の反応式
Cl.Cl.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([C@@:24]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])[CH3:25])=[CH:23][C:16]=3[N:15]=2)=[CH:8][CH:7]=1)(=[NH:5])[NH2:4].C(N(CC)CC)C.[CH3:47][C:48]1[CH:65]=[CH:64][C:51]([C:52](OC2C=CC([N+]([O-])=O)=CC=2)=[O:53])=[CH:50][CH:49]=1>C(Cl)Cl>[CH3:47][C:48]1[CH:65]=[CH:64][C:51]([C:52]([NH:5][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][C:22]([C@@:24]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:26]([N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:27])[CH3:25])=[CH:23][C:16]=4[N:15]=3)=[CH:8][CH:7]=2)=[NH:4])=[O:53])=[CH:50][CH:49]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 532509p-Toluic acid, 4-nitrophenyl esterHCID 23381735(r)-2-(4-Amidinophenylaminomethyl)-1-methyl-5-[1-(ethoxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-dihydrochloride

生成物 1

HCID 145816426ethyl 2-[[(2R)-2-[1-methyl-2-[[4-[N-(4-methylbenzoyl)carbamimidoyl]anilino]methyl]benzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A suspension of 0.7 g (1.2 mmol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(ethoxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-dihydrochloride in 25 ml of methylene chloride is combined with 4.0 ml (28 mmol) of triethylamine and 0.8 g (3.0 mmol) of 4-nitrophenyl 4-methyl-benzoate and heated to 50° C. for 3.5 hours, whereupon a clear solution is formed. After cooling, it is washed with sodium bicarbonate solution, saline solution and water, dried over magnesium sulphate and concentrated by evaporation. The crude product is purified on silica gel, eluting with ethyl acetate/ethanol (50:1 and 9:1). The uniform fractions are combined, concentrated by evaporation, triturated with ether, suction filtered and dried.

後処理

  1. customis formed
  2. temperatureAfter cooling
  3. washit is washed with sodium bicarbonate solution, saline solution and water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe crude product is purified on silica gel
  7. washeluting with ethyl acetate/ethanol (50:1 and 9:1)
  8. concentrationconcentrated by evaporation
  9. customtriturated with ether, suction
  10. filtrationfiltered
  11. customdried

出典と根拠

ORDレコード
ord-b94f5f00f196485696769696d4db5805
出典データセット
uspto-grants-2003_07
特許番号
US06593355B2

反応ノート

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