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

HRID 1951492Notes

Reaction equation

HRID 1951492 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-α]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-b48d4bb331fd437ab08c9968f1f4a702
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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