Pyridine → HCID 11360085, compound

HRID 221361Notes

Reaction equation

HRID 221361 reaction equation
N1C=CC=CC=1.[NH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1.[CH2:24]([S:28](Cl)(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:24]([S:28]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1)(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 754301-Butanesulfonyl chlorideHCID 27611434-(5-Piperidin-4-yl-1,2,4-oxadiazol-3-yl)pyridine

Product 1

HCID 11360085HCID 11360085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine (18 μl, 0.22 mmol) and 4-(5-piperidin-4-yl-[1,2,4]oxadiazol-3-yl)pyridine (Example 51, 50 mg, 0.22 mmol) in CH2Cl2 (4 ml) was treated with butane-1-sulfonyl chloride (56 μl, 0.43 mmol). The reaction was stirred at rt for 18 h then quenched with saturated aqueous NaHCO3 (1 ml). The organic phase was separated, dried (MgSO4) and evaporated. The residue was dissolved in EtOAc (5 ml) and extracted into 2M HCl (10 ml). The aqueous phase was then basified using 2M NaOH to pH=8 and extracted with CH2Cl2 (2×10 ml). The combined organic phases were dried (MgSO4) and evaporated to afford the title compound: RT=3.29 min, m/z (ES+)=351.2 [+H]+.

Workup

  1. customthen quenched with saturated aqueous NaHCO3 (1 ml)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in EtOAc (5 ml)
  6. extractionextracted into 2M HCl (10 ml)
  7. extractionextracted with CH2Cl2 (2×10 ml)
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-c15669dce5ff455295c3ac080391fca5
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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