Lithium Hydroxide → 3,4-dihydro-2-quinolone (DHQ) derivative, 10

HRID 1376141

반응식

HRID 1376141 반응식
[Li+].[OH-].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH:15][CH:16]1[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:26][C:27]([O:29]C)=[O:28])[C:17]1=[O:31])=[O:14])=[CH:7]2>O.C1COCC1>[C:27]([CH2:26][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH:16]([NH:15][C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([Cl:3])=[CH:12][CH:11]=3)=[O:14])[C:17]1=[O:31])([OH:29])=[O:28]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 101944715-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

생성물 1

HCID 101266823,4-dihydro-2-quinolone (DHQ) derivative, 10수율 115.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

LiOH (91.5 g, 2.18 mmol) in H2O (2 mL) was added to a stirring solution of 5-chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Example 1; 557 mg, 1.09 mmol) in THF (11 mL) and the reaction was stirred for 3 h. The reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL) and the organic layer was dried (MgSO4), filtered and evaporated. The resultant white foam was triturated with hot Et2O (20 mL) cooled, filtered, dried and collected by filtration to afford the title compound (500 mg, 92%) as a white solid.

후처리

  1. customThe reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant white foam was triturated with hot Et2O (20 mL)
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-76be88ee4ffd47fc93f4fc250063254f
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169927B2

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