Sodium Bicarbonate → 1-{1-[2-(6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamide

HRID 494987노트

반응식

HRID 494987 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[CH2:31][CH:32]=O)[NH:27][C:26](=[O:34])[CH2:25][CH2:24]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[CH2:31][CH2:32][N:1]1[CH2:2][CH2:3][CH:4]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[CH:14]=4)[CH:9]=[CH:8]3)[CH2:5][CH2:6]1)[NH:27][C:26](=[O:34])[CH2:25][CH2:24]2

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 576827861-(piperidin-4-yl)-1H-indole-6-carboxamideHCID 86601606(6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde

생성물 1

HCID 576828961-{1-[2-(6-Methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxamide수율 10.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

100 mg of 1-(piperidin-4-yl)-1H-indole-6-carboxamide and 87 mg of (6-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)acetaldehyde were suspended in 5 ml of methylene chloride. Thereafter, 0.05 ml of acetic acid and 0.13 g of sodium triacetoxyborohydride were added to the reaction solution, and the obtained mixture was stirred at room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with chloroform. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) and by NH silica gel column chromatography (chloroform-methanol), and then reprecipitated from ethyl acetate, so as to obtain 18 mg of the subject compound.

후처리

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol) and by NH silica gel column chromatography (chloroform-methanol)
  5. customreprecipitated from ethyl acetate

출처 및 근거

ORD 기록
ord-d75b66f1b64141e3b6563faeab78cf26
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538123B2

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