Benzenesulfonyl chloride → HCID 67366550, compound

HRID 553504Notes

Reaction equation

HRID 553504 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH2:22])[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.N1CCOCC1.[C:29]1([S:35]([Cl:38])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[ClH:38].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][NH:22][S:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:37])=[O:36])[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8083MorpholineHCID 67367685HCID 67367685, compound

Product 1

HCID 67366550HCID 67366550, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-[3′-(4-fluorophenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethylamine (0.099 g, 0.329 mmol) in dichloromethane (3 mL). Add resin-bound morpholine (0.145 g, 0.362 mmol) and shake at ambient temperature for 10 min. Add benzenesulfonyl chloride (0.064 g, 0.362 mmol)) and shake reaction at room temperature for 18 hr. Filter, concentrate and purify (SCX chromatography, followed by silica gel chromatography, eluting with 0:100 to 10:90 methanol:dichloromethane), to give free base of the title compound (109 mg, 75%). Dissolve the free base of the title compound (0.105 g, 0.238 mmol) in methanol and add a solution of ammonium chloride (0.013 g, 0.238 mmol) in a minimal volume of MeOH. Shake for 18 hr. at ambient temperature and concentrate to give the title compound (114 mg, 100%). MS (ES): m/z=442 [M+H]+.

Workup

  1. customreaction at room temperature for 18 hr
  2. filtrationFilter
  3. concentrationconcentrate
  4. custompurify
  5. wash(SCX chromatography, followed by silica gel chromatography, eluting with 0:100 to 10:90 methanol:dichloromethane)

Sources & evidence

ORD record
ord-7349c5b97a444708ae1761eaab902260
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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