Sodium Bicarbonate → HCID 59398155, compound

HRID 39775Notes

Reaction equation

HRID 39775 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:17])=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][S:25]([C:28]2[CH:37]=[CH:36][C:31]3[O:32][CH2:33][CH2:34][O:35][C:30]=3[CH:29]=2)(=[O:27])=[O:26])[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:17])=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH2:14][N:18]2[CH2:19][CH2:20][CH:21]([NH:24][S:25]([C:28]3[CH:37]=[CH:36][C:31]4[O:32][CH2:33][CH2:34][O:35][C:30]=4[CH:29]=3)(=[O:27])=[O:26])[CH2:22][CH2:23]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 28811022N-(Piperidin-4-yl)-2,3-dihydro-1,4-benzodioxine-6-sulfonamideHCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Product 1

HCID 59398155HCID 59398155, compoundYield 82.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2 mL of dichloromethane solution containing 30 mg of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 39 mg of N-(piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide and 7.4 μl of acetic acid were added and stirred at room temperature for 2 hours. To the reaction mixture, 41 mg of sodium triacetoxyborohydride was added and stirred at the same temperature for 2 hours. Chloroform and water were added, and adjusted to pH 7.8 with aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to give 55 mg of N-(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)-2,3-dihydro-1,4-benzodioxin-6-sulfonamide as a light brown foam.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 2 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-d98971abf46a46c7abf7f562e53d5732
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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