Hydrochloric Acid → N-{[4'-(1H-1,2,4-triazol-3-yl)-3-biphenylyl]methyl}-2,3-dihydro-1H-inden-2-amine hydrochloride

HRID 70343노트

반응식

HRID 70343 반응식
CC(C)(C)C(OC[N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][CH:26]4[CH2:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27]4)[CH:19]=3)=[CH:14][CH:13]=2)=[N:8]1)=O.C[O-].[Na+].CO.[ClH:42].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[ClH:42].[NH:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][CH:26]4[CH2:27][C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:34]4)[CH:19]=3)=[CH:14][CH:13]=2)=[N:8]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 10942334Sodium MethoxideHCID 58276358HCID 58276358, 화합물

생성물 1

HCID 178478204N-{[4'-(1H-1,2,4-triazol-3-yl)-3-biphenylyl]methyl}-2,3-dihydro-1H-inden-2-amine hydrochloride수율 89%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

To a solution of (3-{3′-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-4-biphenylyl}-1H-1,2,4-triazol-1-yl)methyl 2,2-dimethylpropanoate (0.084 g, 0.17 mmol, Example X-3) in EtOH (1.5 mL) was added a 4.37 M solution of NaOMe in MeOH (0.08 mL, 0.35 mmol). The mixture was stirred for 50 min at RT. A 1.2M solution of concentrated HCl in EtOH was added (1.2 mL), and the mixture was heated at 80° C. for 1 h. The reaction mixture was cooled, diluted with water, and basified to a pH of 10 with addition of saturated Na2CO3 (aq). The mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The residue was dissolved in CH2Cl2 and MeOH, and 4N HCl in dioxane was added (0.2 mL). After stirring for 15 min, the precipitate was filtered, washed with CH2Cl2, and dried, affording the title compound as a colorless solid (0.057 g, 89%). (M+H) 367, 1.74 min (LC/MS Method B).

후처리

  1. temperaturethe mixture was heated at 80° C. for 1 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. additionMeOH, and 4N HCl in dioxane was added (0.2 mL)
  9. stirringAfter stirring for 15 min
  10. filtrationthe precipitate was filtered
  11. washwashed with CH2Cl2
  12. customdried

출처 및 근거

ORD 기록
ord-c95571154991458ea8c2bffd26254544
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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