3-Chlorobenzenesulphonyl chloride → 3-Chloro-N-[3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573631Notes

Reaction equation

HRID 573631 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([CH3:12])=[N:6][C:5]=2[S:4][C:3]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CC(C)([O-])C.[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>CN(C=O)C.C(OCC)(=O)C.O>[Cl:25][C:26]1[CH:27]=[C:28]([S:32]([NH:11][C:9]2[CH:8]=[C:7]([CH3:12])[N:6]=[C:5]3[S:4][C:3]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)=[C:2]([CH3:1])[C:10]=23)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23676156Sodium t-butoxideHCID 683237913,6-Dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-amine

Product 1

HCID 532505453-Chloro-N-[3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamideYield 23.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-amine (45 mg, 0.176 mmol) (Description 34) in DMF (1.5 mL) was added sodium tert-butoxide (42.3 mg, 0.441 mmol) and 3-chlorobenzenesulfonyl chloride (0.050 mL, 0.352 mmol). The reaction mixture was stirred at RT under nitrogen for 3 h and then diluted with ethyl acetate (20 mL) and water (30 mL). The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-100% ethyl acetate in DCM was followed by further purification by MDAP (acidic conditions), to afford the title compound (17.8 mg). LCMS (A) m/z: 430 [M+1]+, Rt 1.06 min (acidic), Rt 0.86 min (basic).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer re-extracted with ethyl acetate (2×15 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel
  6. washeluting with a gradient of 0-100% ethyl acetate in DCM
  7. customwas followed by further purification by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-87803cf5e86a405e8fd14c9dc29d25cb
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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