1-(1H-imidazole-1-carboximidoyl)-1H-imidazole → 5-{4-[3-tert-Butylsulfanyl-2-(2,2-dimethyl-propyl)-5-(pyridin-2-ylmethoxy)-indol-1-ylmethyl]-phenyl}-[1,3,4]oxadiazol-2-ylamine

HRID 1948893노트

반응식

HRID 1948893 반응식
[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=2)[N:8]([CH2:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([NH:30][NH2:31])=[O:29])=[CH:26][CH:25]=2)[C:7]=1[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:4])([CH3:3])[CH3:2].C1N=C[N:41](C(N2C=NC=C2)=N)[CH:40]=1>CN(C=O)C>[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=2)[N:8]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]3[O:29][C:40]([NH2:41])=[N:31][N:30]=3)=[CH:32][CH:33]=2)[C:7]=1[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazoleHCID 666145814-[3-tert-Butylsulfanyl-2-(2,2-dimethyl-propyl)-5-(pyridin-2-ylmethoxy)-indol-1-ylmethyl]-benzoic acid hydrazide

생성물 1

HCID 666023035-{4-[3-tert-Butylsulfanyl-2-(2,2-dimethyl-propyl)-5-(pyridin-2-ylmethoxy)-indol-1-ylmethyl]-phenyl}-[1,3,4]oxadiazol-2-ylamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

To 4-[3-tert-Butylsulfanyl-2-(2,2-dimethyl-propyl)-5-(pyridin-2-ylmethoxy)-indol-1-ylmethyl]-benzoic acid hydrazide (0.05 g, 0.10 mmol) in DMF (1 mL) was added C-(Di-imidazol-1-yl)-methyleneamine (0.08 g, 0.50 mmol), and the reaction was heated at 85° C. for 3 hours. The mixture was cooled to room temperature and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel (EtOAc:hexane gradient) to give the desired product.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (EtOAc:hexane gradient)

출처 및 근거

ORD 기록
ord-65e6614b044f4c9da1ac6db96dbddb25
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399666B2

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