Hydrochloric Acid → HCID 59398349, compound

HRID 39808Notes

Reaction equation

HRID 39808 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:27])=[CH:8][C:9](=[O:26])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1.[O:28]1[C:33]2[CH:34]=[CH:35][C:36]([CH2:38][CH:39]=O)=[CH:37][C:32]=2[O:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>O.C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:28]1[C:33]2[CH:34]=[CH:35][C:36]([CH2:38][CH2:39][N:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[C:7]([CH3:27])=[CH:8][C:9]4=[O:26])[CH:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17]3)=[CH:37][C:32]=2[O:31][CH2:30][CH2:29]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 17979906HCID 17979906, compoundHCID 59398295HCID 59398295, compound

Product 1

HCID 59398349HCID 59398349, compoundYield 68.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.4 mL of dichloromethane solution containing 89 mg of ethyl 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate and 94 mg of (2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde, 24 μL of acetic acid was added and stirred at room temperature for 30 min. To the reaction mixture, 76 mg of sodium triacetoxyborohydride was added, and stirred at room temperature for 1 hour. To the reaction mixture, chloroform and water were added, and adjusted to pH 1 with 6 mol/L hydrochloric acid. The organic layer was separated, and adjusted to pH 13 by adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer, thereafter 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=50:1], to give 87 mg of ethyl 4-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate as a colorless oil.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 1 hour
  3. customThe organic layer was separated
  4. additionby adding 5 mol/L aqueous sodium hydroxide solution to the aqueous layer
  5. extractionextracted with chloroform
  6. washwashed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-c5962f55e1c34cb39e928df12514f8b4
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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