Pyrrolidine → HCID 15521565, compound

HRID 413024Notes

Reaction equation

HRID 413024 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([N:21]2[CH2:24][CH:23]([NH:25][S:26]([C:29]3[CH:34]=[C:33](F)[CH:32]=[C:31]([F:36])[CH:30]=3)(=[O:28])=[O:27])[CH2:22]2)[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1>CS(C)=O.ClCCl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:21]2[CH2:22][CH:23]([NH:25][S:26]([C:29]3[CH:34]=[C:33]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:32]=[C:31]([F:36])[CH:30]=3)(=[O:27])=[O:28])[CH2:24]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 15521564HCID 15521564, compound

Product 1

HCID 15521565HCID 15521565, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

0.104 cm3 of pyrrolidine is added, at room temperature, to 0.24 g of N-{-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}-(3,5-difluorophenyl)sulfonamide in solution in 6 cm3 of dimethyl sulfoxide and then the mixture is heated for 18 hours at 90° C. The reaction mixture is diluted with 30 cm3 of dichloromethane and washed with three times 30 cm3 of distilled water. The organic phased is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by flash chromatography on silica gel, eluting with dichloromethane. 50 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-(3-fluoro-5-pyrrolidin-1-ylphenyl)sulfonamide are thus obtained in the form of a white powder [1H NMR spectrum (600 MHz, CDCl3 with addition of a few drops of CD3COOD d4, δ in ppm): 2.04 (mt: 4H); from 3.20 to 3.35 (mt: 6H); 3.60 (t, J=8.5 Hz: 2H); 4.14 (mt: 1H); 4.57 (s: 1H); 6.31 (broad d, J=11.5 Hz: 1H); 6.70 (broad d, J=8.5 Hz: 1H); 6.72 (broad s: 1H); from 7.20 to 7.35 (mt: 8H)].

Workup

  1. washwashed with three times 30 cm3 of distilled water
  2. dry with materialThe organic phased is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5df35634a23747a9a43656d059c4be3f
Source dataset
uspto-grants-2003_05
Patent number
US06566356B2

Reaction notes

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