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 494987Notes

Reaction equation

HRID 494987 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d75b66f1b64141e3b6563faeab78cf26
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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