Potassium Carbonate → HCID 9934326, compound

HRID 487602Notes

Reaction equation

HRID 487602 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]1)[C:5]2=[O:29].[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.CN(C)C=O>[C:23]1([C:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:6]3[C:5](=[O:29])[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[CH:3]=4)[NH:8][C:7]3=[O:12])[CH2:18][CH:19]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 19092327HCID 19092327, compound

Product 1

HCID 9934326HCID 9934326, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-amino-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-1,2,3,4-tetrahydroquinazoline-2,4-dione (390 mg), methanesulfonyl chloride (229 mg), potassium carbonate (276 mg) and dry N,N-dimethylformamide (10 ml) was stirred for 1 hour at room temperature. The mixture was poured into water, neutralized with 1N sodium hydroxide and extracted with ethyl acetate, and the extract was washed with brine. The organic layer was dried and evaporated. The crude residue was chromatographed on a silica gel (50 g), eluting with 10% methanol in dichloromethane to give 3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-6-methylsulfonylamino-1,2,3,4-tetrahydroquinazoline-2,4-dione (292 mg). Recrystallization from ethyl acetate gave a crystal thereof (202 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with brine
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe crude residue was chromatographed on a silica gel (50 g)
  6. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-700770fe6df4403c8fef66828086175e
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

Loading…