Dimethylamine → HCID 58504091, compound

HRID 2407722Notes

Reaction equation

HRID 2407722 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[S:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH3:18][NH:19][CH3:20]>O1CCCC1>[CH3:18][N:19]([CH2:2][C:3]1[N:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[S:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH3:20]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58504032HCID 58504032, compound

Product 1

HCID 58504091HCID 58504091, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound prepared in Example 152 (500 mg) and dimethylamine (1.8 mL) in tetrahydrofuran (3 mL) was stirred at room temperature for 30 minutes. The mixture was partitioned between a saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1 then ethyl acetate=1) to obtain the title compound (191 mg) having the following physical data. 1H NMR (CDCl3): δ 8.63-8.59 (m, 1H), 8.34-8.25 (m, 1H), 7.84-7.76 (m, 1H), 7.40-7.33 (m, 1H), 4.01 (s, 2H), 3.91 (m, 3H), 2.41 (s, 6H);

Workup

  1. customThe mixture was partitioned between a saturated aqueous sodium bicarbonate solution and ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-3da8e64e47c74dcea1f974a8aa6ae6af
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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