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 2089278

반응식

HRID 2089278 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매3회

반응 조건

온도
2 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-949239e502294078944066e64d5ff91f
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436034B2

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