Ethanol hydrochloride → 7-[(3S)-3-(Dimethylamino)pyrrolidinyl]-5-methyl-6-phenyl-2-(2-phenylethyl)-1,3-benzoxazole-4-carbonitrile

HRID 17351

反応式

HRID 17351 の反応式
[CH3:1][N:2]([CH3:34])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:10]([CH3:27])[C:11]([C:25]#[N:26])=[C:12]3[C:16]=2[O:15][C:14](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:13]3)[CH2:4]1.Cl.C(O)C.[H][H]>C(O)C>[CH3:34][N:2]([CH3:1])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:10]([CH3:27])[C:11]([C:25]#[N:26])=[C:12]3[C:16]=2[O:15][C:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:13]3)[CH2:4]1

参加物

5

反応物 3

HCID 21887872Ethanol hydrochlorideHCID 685865437-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 685871117-[(3S)-3-(Dimethylamino)pyrrolidinyl]-5-methyl-6-phenyl-2-(2-phenylethyl)-1,3-benzoxazole-4-carbonitrile収率 16.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile (I-93) (100 mg, 0.22 mmol) and 1 N hydrochloric acid/ethanol solution (223 μl, 10.22 mmol) were dissolved in ethanol (2 ml), 10% carbon-held palladium catalyst was added, followed by stirring at room temperature under atmospheric pressure of hydrogen for 3 hours. After filtration through Celite, the solvent was concentrated under reduced pressure, ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution were added to make the aqueous layer basic, followed by fractionation. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away, the resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (20:1, v/v), recrystallized and purified with n-hexane/ethyl acetate/diisopropyl ether to obtain the entitled compound (16 mg, 16%) as a white solid.

後処理

  1. addition10% carbon-held palladium catalyst was added
  2. filtrationAfter filtration through Celite
  3. concentrationthe solvent was concentrated under reduced pressure, ethyl acetate
  4. additionan aqueous saturated sodium hydrogencarbonate solution were added
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated away
  8. washeluted with a mixed solvent of chloroform/methanol (20:1
  9. customv/v), recrystallized
  10. custompurified with n-hexane/ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-0ba5f161a0894d1f84113a168ccd6a5b
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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