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

HRID 573689Notes

Reaction equation

HRID 573689 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>CO>[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 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 115) (98 mg, 0.206 mmol) in 37% HCl (2 mL, 24.35 mmol) was heated to 100° C. under nitrogen atmosphere overnight. The reaction mixture was cooled to RT, diluted with MeOH and concentrated in vacuo. The residue was purified by MDAP (acidic conditions), to afford the title compound (58 mg). LCMS (A) m/z: 461 [M+1]+, Rt 1.27 min (acidic).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-7c2a0a19392e407a89c55d58db8ba1de
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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