Hydrochloric Acid → 3-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamide

HRID 573690Notes

Reaction equation

HRID 573690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:18]C)[N:15]=[C:14]3[S:20][C:21]([CH3:31])=[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)=[C:21]([CH3:31])[S:20][C:14]=3[NH:15][C:16](=[O:18])[CH:17]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 683237633-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

Product 1

HCID 683238243-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, a solution of 3-chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 115) (710 mg, 1.495 mmol) in 37% HCl (8 mL, 97 mmol) was heated to 100° C. under nitrogen atmosphere overnight. The reaction mixture was cooled to RT, diluted with DCM (ca. 50 mL) and washed with water (ca. 50 mL×2). The combined aqueous layer was re-extracted with DCM (ca. 25 mL) and the combined organic layers passed through phase separator and the solvent concentrated in vacuo. The residue was further triturated with DCM, to afford the title compound (407 mg).

Workup

  1. washwashed with water (ca. 50 mL×2)
  2. extractionThe combined aqueous layer was re-extracted with DCM (ca. 25 mL)
  3. concentrationthe solvent concentrated in vacuo
  4. customThe residue was further triturated with DCM

Sources & evidence

ORD record
ord-d8673b562dac4012a33348128e2f778a
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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