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

HRID 17351
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HRID 17351 반응식
[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
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참가 물질

5

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ba5f161a0894d1f84113a168ccd6a5b
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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