Sodium Carbonate → (E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

HRID 333949Notes

Reaction equation

HRID 333949 reaction equation
O[CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6].C(N(S(F)(F)[F:31])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:31][CH:2]([CH3:24])/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 86691596(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

Product 1

HCID 56949080(E)-4-Fluoro-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(E)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (32.5 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (200 μl) and added to a solution of (diethylamino)sulphur trifluoride (DAST; 19 μl, 0.12 mmol) in 200 μl dichloromethane. The mixture was stirred for 30 minutes at room temperature, additional DAST was added (10 μl, 0.063 mmol) and stirring was continued for additional 30 minutes. Solid sodium carbonate (25 mg) was added, the mixture was filtered, the filtrate evaporated to dryness and the residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 4 mg (0.012 mmol, 12%).

Workup

  1. stirringstirring
  2. waitwas continued for additional 30 minutes
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customthe residue purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  6. customto yield 4 mg (0.012 mmol, 12%)

Sources & evidence

ORD record
ord-6bf75af861a74a5d9256c2e2ffcf0118
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

Loading…