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

HRID 471876ノート

反応式

HRID 471876 の反応式
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

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 10942334Sodium MethoxideHCID 58276358HCID 58276358、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7d36806915264b38b7b5808afa1a06e7
出典データセット
uspto-grants-2014_01
特許番号
US08633175B2

反応ノート

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