Pyridine → HCID 68684032, compound

HRID 2234983Notes

Reaction equation

HRID 2234983 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([NH2:15])[C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)[CH2:3]1.N1C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:15][C:13]2[C:12]([O:16][CH3:17])=[CH:11][CH:10]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[N:14]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 58988130HCID 58988130, compound

Product 1

HCID 68684032HCID 68684032, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-[(3R,5S)-3,5-Dimethyl-1-piperazinyl]-3-(methyloxy)-2-pyridinamine (D7, Method E)(1.5 g, 6.35 mmol) was dissolved in DCM (15 mL) and pyridine (15 mL) and then cooled to 0° C. 4-Bromobenzenesulfonyl chloride (3.04 g, 11.9 mmol), dissolved in DCM (8 mL) was then added dropwise and the reaction then allowed to warm to room temperature overnight. The reaction was then evaporated to a minimum and redissolved in DCM (100 mL) and washed with water (50 mL). Aqueous layer was extracted with DCM (100 mL) and combined organic extracts washed with saturated sodium hydrogen carbonate (2×100 mL) and brine (100 mL). The organic layer was dried (MgSO4) and evaporated to give a brown solid which was triturated with ethyl acetate (3×10 mL) to give the title compound as a pale yellow powder (D17) (1.382 g). MS (ES+) m/e 455/457 [M+H]+.

Workup

  1. additionwas then added dropwise
  2. customthe reaction
  3. customThe reaction was then evaporated to a minimum
  4. dissolutionredissolved in DCM (100 mL)
  5. washwashed with water (50 mL)
  6. extractionAqueous layer was extracted with DCM (100 mL)
  7. washcombined organic extracts washed with saturated sodium hydrogen carbonate (2×100 mL) and brine (100 mL)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated
  10. customto give a brown solid which
  11. customwas triturated with ethyl acetate (3×10 mL)

Sources & evidence

ORD record
ord-152d0297172d4ad192298a1e667f4495
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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