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

HRID 1422527ノート

反応式

HRID 1422527 の反応式
[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

参加物

9

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 176Acetic Acid触媒HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d9c65f760be242fc838fe0803f9a3c99
出典データセット
uspto-grants-2015_01
特許番号
US08927484B2

反応ノート

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