1-Pentanesulfonyl chloride → HCID 11386162, compound

HRID 1689845Notes

Reaction equation

HRID 1689845 reaction equation
[CH2:1]([S:6](Cl)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:19][CH2:18]2)=[N:15][CH:16]=1>N1C=CC=CC=1.ClCCl>[F:34][C:31]([F:32])([F:33])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[N:15]=[CH:16][C:11]([NH:10][S:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:8])=[O:7])=[CH:12][CH:13]=2)[CH2:22][CH2:21]1)=[O:24]

Participants

5

Reactant 2

HCID 2375551-Pentanesulfonyl chlorideHCID 66905728HCID 66905728, compound

Product 1

HCID 11386162HCID 11386162, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-Pentanesulfonyl chloride (0.034 g, 0.30 mmol) was added slowly to a solution of [4-(5-aminopyridin-2-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone in pyridine (2 mL) at 0° C. The mixture was stirred at 25° C. for 16 hours and then diluted with dichloromethane. The organic phase was washed with water and saturated NaCl solution, dried over anhydrous MgSO4. After removal of dichloromethane, the product was purified by column chromatography to afford the title compound in 4% yield (2.7 mg). 1H NMR (300 MHz, CDCl3) δ 8.02, 7.87, 7.74, 7.61, 7.36, 6.94, 4.47, 4.11, 3.87, 3.68, 3.60, 3.42, 2.99, 1.77, 1.32, 0.88. MS (ES+) m/z 485.2 (M+1).

Workup

  1. washThe organic phase was washed with water and saturated NaCl solution
  2. dry with materialdried over anhydrous MgSO4
  3. customAfter removal of dichloromethane
  4. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-ef664399341d44b5a0c1e74083654245
Source dataset
uspto-grants-2012_04
Patent number
US08153636B2

Reaction notes

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