Dicyclohexylcarbodiimide → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

HRID 1073707노트

반응식

HRID 1073707 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.NC1N=CC2C=CC=CC=2N(CCOC2CCCCO2)C1=O.[C:60]1([C:66]2[C:72]3[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=3[N:70]([CH2:77][CH2:78][O:79][CH:80]3[CH2:85][CH2:84][CH2:83][CH2:82][O:81]3)[C:69](=[O:86])[CH:68]([NH2:87])[N:67]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C(Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:87][CH:68]1[N:67]=[C:66]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=2[N:70]([CH2:77][CH2:78][O:79][CH:80]2[CH2:85][CH2:84][CH2:83][CH2:82][O:81]2)[C:69]1=[O:86])=[O:12]

참가 물질

7

반응물 5

HCID 10868DicyclohexylcarbodiimideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 14800304(3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((RS)-2-tetrahydropyranyloxy) ethyl}-2H-1,4-benzodiazepine-2-oneHCID 70360821amino-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

생성물 1

HCID 14800305(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a mixture of indole-2-carboxylic acid (0.19 g), N-hydroxybenzotriazole (0.16 g) and N,N'-dicyclohexylcarbodiimide (0.24 g) in chloroform (10 ml) was added amino-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4- benzodiazepine-2-one and (3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((SR) -2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one at ambient temperature under stirring. The mixture was stirred for 2 hours under the same conditions. The resultant precipitate was filtered off. The combined filtrate and washings were evaporated under reduced pressure and the residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1) to give a mixture (white powder, 0.45 g) of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino) -5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one and (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((SR) -2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine- 2-one.

후처리

  1. stirringThe mixture was stirred for 2 hours under the same conditions
  2. filtrationThe resultant precipitate was filtered off
  3. customThe combined filtrate and washings were evaporated under reduced pressure
  4. additionthe residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-ff40c51532d449bc8529127a5cefbaa3
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04970207

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