5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → 5-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethanesulfonyl-benzenesulfonylamino)phenyl]-amide

HRID 730211Notes

Reaction equation

HRID 730211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[C:16]([S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:25][CH3:26])(=[O:11])=[O:10].[Cl:27][C:28]1[CH:41]=[CH:40][C:31]2[S:32][C:33]([S:36](Cl)(=[O:38])=[O:37])=[C:34]([CH3:35])[C:30]=2[CH:29]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:26][O:25][C:13]1[CH:14]=[CH:15][C:16]([S:18]([C:21]([F:24])([F:22])[F:23])(=[O:20])=[O:19])=[CH:17][C:12]=1[S:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:36]([C:33]1[S:32][C:31]2[CH:40]=[CH:41][C:28]([Cl:27])=[CH:29][C:30]=2[C:34]=1[CH3:35])(=[O:38])=[O:37])(=[O:10])=[O:11]

Participants

5

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 68948452N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide

Product 1

HCID 115419905-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethanesulfonyl-benzenesulfonylamino)phenyl]-amideYield 61.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of of N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide (0.5 mmol, prepared as in Example A) in DCM (1 mL) and pyridine (1 mL), 5-chloro-3-methylbenzo[b]thiophene-2-sulfonyl chloride (0.55 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to afford 202 mg of 5-chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-trifluoromethanesulfonyl-benzenesulfonylamino)phenyl]-amide. LC: Tr 1.32 min, MS: 655.4 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 2.14 (s, 3H), 4.29 (s, 3H), 6.33 (bs, 1H), 6.54 (d, 1H), 6.98 (t, 1H), 7.24 (t, 1H), 7.35 (d, 1H), 7.45 (dd, 1H), 7.49 (dd, 1H), 7.70 (d, 1H), 7.75 (d, 1H), 8.14 (bs, 1H), 8.17 (dd, 1H), 8.31(d, 1H) ppm.

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-75f509c4f6d146dd82bf3998daa5e935
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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