1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[3-Amino-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxamide

HRID 12427

反応式

HRID 12427 の反応式
C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[C:22]1([C:28]2[N:29]=[CH:30][N:31]([C:33]3[C:38]([C:39]([OH:41])=O)=[CH:37][CH:36]=[CH:35][N:34]=3)[CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[NH2:43][CH:44]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH:45]([OH:49])[C:46]([NH2:48])=[O:47].C([O-])(O)=O.[Na+]>ClCCl.CCN(CC)CC>[NH2:48][C:46](=[O:47])[CH:45]([OH:49])[CH:44]([NH:43][C:39]([C:38]1[C:33]([N:31]2[CH:32]=[C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:29]=[CH:30]2)=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:41])[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 225938833-Amino-2-hydroxy-4-phenylbutanamide hydrochlorideHCID 667200892-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 66720082N-[3-Amino-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxamide収率 37.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒3 回

反応条件

温度
2 °C

実験手順

0.75 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 0.51 g of hydroxylbenzotriazole (HOBt) and 0.55 ml of triethylamine (Et3N) were successively added to a solution of 1.0 g of 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylic acid (3.77 mmol) in 50 ml of dichloromethane at 0-4° C., and the mixture was stirred at 0-4° C. for 1 hour. 0.9 g of 3-amino-2-hydroxy-4-phenylbutanamide hydrochloride (3.9 mmol) and 0.55 ml of Et3N were then added and, after about 5 minutes, a pH of 8-9 was adjusted by adding 0.5 ml of Et3N. The mixture was stirred at 0-4° C. for 1 hour and then at room temperature overnight. 50 ml of saturated NaHCO3 solution were then added to the mixture, and the organic phase was separated off. Drying and evaporating the solvent resulted in 620 mg of a reddish oil, which was reacted further immediately without further purification.

後処理

  1. stirringThe mixture was stirred at 0-4° C. for 1 hour
  2. customat room temperature
  3. customovernight
  4. customthe organic phase was separated off
  5. customDrying
  6. customevaporating the solvent

出典と根拠

ORDレコード
ord-6b46d268ecdb4ada8a7b6d15fb708a7b
出典データセット
uspto-grants-2010_06
特許番号
US07728012B2

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