Hydrochloric Acid → 4-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochloride

HRID 352107노트

반응식

HRID 352107 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]I)[CH:3]=1.[CH2:22]([NH:24][CH2:25][CH2:26][OH:27])[CH3:23].Cl>O1CCCC1.C(OCC)C.ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][N:24]([CH2:22][CH3:23])[CH2:25][CH2:26][OH:27])[CH:3]=1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 80722-(Ethylamino)ethanolHCID 698282664-Chloro-2-[[(1r)-4-iodo-1-phenylbutyl]oxy]benzonitrile

생성물 1

HCID 698289354-Chloro-2-[[(1R)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutyl]oxy]-benzonitrile hydrochloride수율 65.4%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 21881112Ethyl ether methylene chloride용매

실험 절차

A solution of the product from Example 1 step (c) (200 mg) and 2-(ethylamino)ethanol (163 mg, 0.14 ml) in tetrahydrofuran (5 ml) was stirred for 2 days. The solvent was removed in vacuo and the residue dissolved in water and aqueous potassium carbonate and extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give an oil. To a solution of this amine in diethyl ether-dichloromethane was added a 1M solution of hydrogen chloride in diethyl ether. The crystals that formed were collected and dried to afford the title compound as a white solid (65 mg). M.p. 141-144° C.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionaqueous potassium carbonate and extracted with ethyl acetate (three times)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil
  8. customThe crystals that formed
  9. customwere collected
  10. customdried

출처 및 근거

ORD 기록
ord-1479a23a332f49c69d0922977bfafd6d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743939B2

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