Propanal → 2-methyl-4-[4-[(E)-pent-1-enyl]sulfonylpiperazin-1-yl]quinoline

HRID 333934Notes

Reaction equation

C(OP([CH2:9][S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])(OCC)=O)C.[Br-].[Li+].C(=O)CC.[CH2:36]1[CH2:46]CN2C(=NCCC2)[CH2:38][CH2:37]1>C1COCC1.ClCCl>[CH3:29][C:21]1[CH:20]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([S:10](/[CH:9]=[CH:46]/[CH2:36][CH2:37][CH3:38])(=[O:12])=[O:11])[CH2:18][CH2:17]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

Conditions

Temperature: -10 °C

Procedure

4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline (47 mg, 0.106 mmol) was dissolved in anhydrous THF (1 ml), lithium bromide (11.1 mg, 0.128 mmol) and propionaldehyde (9.2 μl, 0.128 mmol) were added with stirring and the mixture was cooled to −10° C. DBU (15.2 μl, 0.102 mmol) was added, and the temperature was raised to room temperature. Stirring was continued for 30 minutes, the reaction mixture was diluted with dichloromethane, washed with 5% sodium bicarbonate solution (2×), water and evaporated to dryness. The residue was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile). 5 mg of a solid were obtained (0.014 mmol, 14%).

Workup

temperaturethe temperature was raised to room temperature
stirringStirring
washwashed with 5% sodium bicarbonate solution (2×), water
customevaporated to dryness
customThe residue was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile)

Sources & evidence

ORD record: ord-fcc0a5ed81fd48d980d45a3625a6b33a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Reaction notes

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