Methanol → HCID 59398190, compound

HRID 2193320Notes

Reaction equation

HRID 2193320 reaction equation
CO.[C:3]([O:7][C:8](=[O:41])[N:9]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]2[O:35][CH2:36][CH2:37][O:38][C:33]=2[CH:32]=1)[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]2[C:27]3[C:22](=[C:23]([NH2:28])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]2=[O:29])[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].[C:42](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>O>[C:3]([O:7][C:8](=[O:41])[N:9]([CH2:30][C:31]1[CH:40]=[CH:39][C:34]2[O:35][CH2:36][CH2:37][O:38][C:33]=2[CH:32]=1)[CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][N:18]2[C:27]3[C:22](=[C:23]([NH:28][CH3:42])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]2=[O:29])[CH2:14][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

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-a21918955ec646c0abdb5e574594d0c6
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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