Morpholine → 4,8-Dichloro-2-(2-isopropyl-thiazol-4-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline

HRID 1422527노트

반응식

HRID 1422527 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:19])[C:8]([O:12][CH2:13][CH:14](OC)OC)=[CH:9][CH:10]=2)[N:5]=[C:4]([C:20]2[N:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[S:23][CH:24]=2)[CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.Cl.CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:19])[C:8]([O:12][CH2:13][CH2:14][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:9][CH:10]=2)[N:5]=[C:4]([C:20]2[N:21]=[C:22]([CH:25]([CH3:26])[CH3:27])[S:23][CH:24]=2)[CH:3]=1

참가 물질

9

반응물 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 582896314,8-Dichloro-7-(2,2-dimethoxy-ethoxy)-2-(2-isopropyl-thiazol-4-yl)-quinoline

생성물 1

HCID 582895734,8-Dichloro-2-(2-isopropyl-thiazol-4-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline수율 86%

시약·촉매·용매 5

HCID 176Acetic Acid촉매HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

4,8-Dichloro-7-(2,2-dimethoxy-ethoxy)-2-(2-isopropyl-thiazol-4-yl)-quinoline (250 mg, 0.565 mmol) was dissolved in AcOH (5.0 mL) and 2N HCl(aq). The reaction mixture was placed in a 60° C. oil bath and stirred for 1 h. Remove solvent under reduced pressure. The crude material was taken up in EtOAc and washed with ½ sat NaHCO3(aq). Organics were dried over Na2SO4, filtered and was concentrated. The crude material was then taken up in CH2Cl2. Morpholine (77 μL, 0.88 mmol) was added to the reaction mixture and stirred for 15 min. NaBH(OAc)3 (161 mg, 0.761 mmol) and AcOH (1 drop) were added and the reaction was monitored by LC/MS. After 5 min the reaction was determined to be complete. The mixture was diluted with DCM and washed with ½ sat brine, dried with Na2SO4, filtered and was concentrated. 4,8-dichloro-2-(2-isopropyl-thiazol-4-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline (218 mg, 86%) was isolated by silica gel chromatography as a yellow solid.

후처리

  1. customwas placed in a 60° C.
  2. washwashed with ½
  3. dry with materialOrganics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationwas concentrated
  6. stirringstirred for 15 min
  7. waitAfter 5 min the reaction was determined
  8. washwashed with ½
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-d9c65f760be242fc838fe0803f9a3c99
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927484B2

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