Sodium Carbonate → HCID 67170312, compound

HRID 2040233Notes

Reaction equation

HRID 2040233 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>CN(C)C=O>[CH3:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][N:13]1[CH2:14][CH2:15][C@@H:11]([NH:10][C:9]2[CH:8]=[CH:7][C:6]([S:16]([NH2:19])(=[O:17])=[O:18])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 67126429HCID 67126429, compound

Product 1

HCID 67170312HCID 67170312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-3-nitro-4-(pyrrolidin-3-ylamino)benzenesulfonamide (440 mg) in N,N-dimethylformamide (10 mL) was added sodium carbonate (132 mg) and 1-bromo-2-(2-methoxyethoxy)ethane (0.155 mL). The reaction mixture was heated at 60° C. for 18 hours and after an aqueous workup, the crude product was purified on silica gel with a 2.5-10% methanol in methylene chloride gradient to provide the title compound.

Workup

  1. customafter an aqueous workup, the crude product was purified on silica gel with a 2.5-10% methanol in methylene chloride gradient

Sources & evidence

ORD record
ord-68bb650c1f7f4b9a93428e7d8b3dae8c
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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