Sodium Carbonate → N-(2,6-difluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

HRID 421757Notes

Reaction equation

HRID 421757 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH2:14]1[NH:19][CH2:18][CH2:17][N:16]2[CH2:20][CH2:21][CH2:22][C@@H:15]12.C(=O)([O-])[O-].[Na+].[Na+].[F:29][C:30]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:31]=1[NH2:32]>ClCCl>[F:29][C:30]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:31]=1[NH:32][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([N:19]2[CH2:18][CH2:17][N:16]3[CH2:20][CH2:21][CH2:22][C@H:15]3[CH2:14]2)=[O:9])[CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 796472,6-DifluoroanilineHCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonane

Product 1

HCID 46853383N-(2,6-difluorophenyl)-3-[(8aS)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-(chlorosulfonyl)benzoyl chloride (0.474 g, 1.98 mmol) in anhydrous dichloromethane (10 mL) was added (S)-octahydropyrrolo[1,2-a]pyrazine (0.250 g, 1.98 mmol) in dichloromethane (4 mL) slowly over 10 minutes at room temperature. Then sodium carbonate (0.420 g, 3.96 mmol) was added. The mixture was stirred at room temperature for 5 hours. Then 2,6-difluoroaniline (2.56 g, 19.81 mmol) was added. The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by chromatography on silica gel (dichloromethane, then methanol/dichloromethane=1:10) to give the title compound.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (dichloromethane

Sources & evidence

ORD record
ord-ff1625a4393e4d629871f2b52a661c4f
Source dataset
uspto-grants-2012_01
Patent number
US08101614B2

Reaction notes

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