홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Cyanogen Bromide → 5-(4-{1,2-Dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}phenyl)-1,3,4-oxadiazol-2-amine

HRID 1025810
노트
인쇄 미리보기

반응식

HRID 1025810 반응식
O.[NH2:2][NH2:3].[CH3:4][C:5]([C:25]1[CH:34]=[CH:33][C:28]([C:29](OC)=[O:30])=[CH:27][CH:26]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH3:17])=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+].[N:40]#[C:41]Br>C(O)C.O1CCOCC1.O>[CH3:4][C:5]([C:25]1[CH:26]=[CH:27][C:28]([C:29]2[O:30][C:41]([NH2:40])=[N:3][N:2]=2)=[CH:33][CH:34]=1)([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]([CH3:17])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH3:24])=[CH:13][CH:14]=1)[CH:6]([CH3:8])[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10476Cyanogen BromideHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium Bicarbonate2회HCID 59026736Methyl 4-{1,2-dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}benzoate2회

생성물 1

HCID 583812355-(4-{1,2-Dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}phenyl)-1,3,4-oxadiazol-2-amine

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

Hydrazine monohydrate (10 equiv.) is added to a stirred solution of 5g (1 equiv.) in ethanol and the resulting solution heated at reflux until 5g is consumed. After cooling to room temperature, the volatiles are removed in vacuo, and the residue is partitioned between EtOAc and water. The organic phase is separated, washed three times with water, brine, dried (MgSO4) and concentrated in vacuo. The crude residue is dissolved in dioxane to which aqueous sodium bicarbonate (1.1 equiv) in water is added dropwise via syringe. A solution of cyanogen bromide (1.1 equiv.) in dioxane is then added slowly, and the resulting mixture is aged at ambient temperature until the reaction is deemed complete. The reaction mixture is poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5h. If desired, 5h can be resolved into its enantiomeric components using preparative chiral HPLC techniques.

후처리

  1. temperaturethe resulting solution heated
  2. customis consumed
  3. customthe volatiles are removed in vacuo
  4. customthe residue is partitioned between EtOAc and water
  5. customThe organic phase is separated
  6. washwashed three times with water, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. additionis added dropwise via syringe
  10. customis aged at ambient temperature until the reaction
  11. extractionextracted three times with EtOAc
  12. washThe combined organic extracts are washed with brine
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated in vacuo
  15. customPurification of the crude residue by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-57d36fc2316b482795a533dbe76d6aa2
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729104B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트