(3-Bromopropyl)benzene → HCID 23077654, compound

HRID 1349512Notes

Reaction equation

HRID 1349512 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:25])[C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[CH:12][N:13]2[CH2:18][CH2:17][NH:16][C:15](=[O:19])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([CH2:32][CH2:33][CH2:34]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H-].[Na+].S([O-])(O)(=O)=O.[K+]>CS(C)=O>[CH2:1]([O:8][C:9]1[C:10](=[O:25])[C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:34][CH2:33][CH2:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:19])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 23077478HCID 23077478, compound

Product 1

HCID 23077654HCID 23077654, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9-Benzyloxy-7-(thiazol-2-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (30 mg) and 3-phenylpropyl bromide (0.02 ml) were added to dimethyl sulfoxide (1 ml), and sodium hydride (7 mg) was added with stirring. After stirring for 20 min, 5% aqueous potassium hydrogen sulfate solution was added and the mixture was extracted twice with ethyl acetate. The ethyl acetate layer was washed with brine, dried, concentrated, and subsequently purified by silica gel thin layer chromatography (chloroform-methanol=15:1) to give 9-benzyloxy-2-(3-phenylpropyl)-7-(thiazol-2-yl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (27 mg).

Workup

  1. additionwas added
  2. stirringAfter stirring for 20 min
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customsubsequently purified by silica gel thin layer chromatography (chloroform-methanol=15:1)

Sources & evidence

ORD record
ord-c465e67007e34ef1a0d00d556d63a0a5
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

Loading…