Benzenesulfonamide → 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-N-(phenylsulphonyl)-2-pyridinecarboxamide

HRID 2356621Notes

Reaction equation

HRID 2356621 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15](O)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[C:28]1([S:34]([NH2:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([NH:37][S:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:36])=[O:35])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11495634Gsk-269984B

Product 1

HCID 117208866-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-N-(phenylsulphonyl)-2-pyridinecarboxamideYield 42.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-2-pyridinecarboxylic acid (81 mg) in dichloromethane (2 ml) and tetrahydrofuran (2 ml) was added benzenesulphonamide (50 mg), 4-dimethyl-aminopyridine (3.5 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (61 mg) and the mixture stirred at ambient temperature for 5 hours. Solvent was removed in vacuo and water (5 ml) added. The mixture was extracted with ether (2×5 ml) and the combined extracts dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (46 mg, 42%) as a white solid. LC/MS [MH+]=545/547, Rt=3.89 min.

Workup

  1. customSolvent was removed in vacuo and water (5 ml)
  2. additionadded
  3. extractionThe mixture was extracted with ether (2×5 ml)
  4. dry with materialthe combined extracts dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by mass-directed autopreparation

Sources & evidence

ORD record
ord-8045e4892af54e048d7176d507930e0b
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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