Ammonium Chloride → 2-Methyl-propane-2-sulfinic acid {1-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-ethyl}-amide

HRID 420525Notes

Reaction equation

HRID 420525 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](/[CH:18]=[N:19]/[S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1.[CH3:26][Mg]Br.[NH4+].[Cl-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH:18]([NH:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH3:26])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 57906558HCID 57906558, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 666593872-Methyl-propane-2-sulfinic acid {1-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-ethyl}-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid 1-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-meth-(E)-ylideneamide (20 mg, 0.045 mmol) in anhydrous THF (0.5 mL) was added methylmagnesium bromide (3 M solution in Et2O, 0.045 mL, 0.14 mmol) at RT. The reaction mixture was stirred for 3 h30 then poured into a saturated solution of NH4Cl in water and extracted with AcOEt. The organic layer was dried over Na2SO4, filtered and evaporated to dryness to give the crude 2-methyl-propane-2-sulfinic acid {1-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-ethyl}-amide intermediate.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ebe3fcae228e44cd95f4b5515fe6f0bf
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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