Methanol → HCID 59398190, compound

HRID 39941Notes

Reaction equation

HRID 39941 reaction equation
CO.[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]([CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N:30]4[C:39]5[C:34](=[C:35]([NH2:40])[CH:36]=[CH:37][CH:38]=5)[CH:33]=[CH:32][C:31]4=[O:41])[CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1.[C:42](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>O>[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]([CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N:30]4[C:39]5[C:34](=[C:35]([NH:40][CH3:42])[CH:36]=[CH:37][CH:38]=5)[CH:33]=[CH:32][C:31]4=[O:41])[CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 59397938HCID 59397938, compound

Product 1

HCID 59398190HCID 59398190, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.5 mL of a methanol solution containing 280 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-amino-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 0.5 mL of water, 83 mg of sodium carbonate and 99 mg of dimethyl sulfate were added, and stirred at room temperature for 3 days. The insoluble material was filtered off, and the solvent was removed under reduced pressure, and purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate: methanol=10:1], to give 65 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-(N-methylamino)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oil.

Workup

  1. additionwere added
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was removed under reduced pressure
  4. custompurified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate: methanol=10:1]

Sources & evidence

ORD record
ord-5d7d800338824720b4f4d0cd9f92cab6
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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