Pyridine → HCID 11484315, compound

HRID 221358Notes

Reaction equation

HRID 221358 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]([O:28][C:29](Cl)=[O:30])[CH:25]([CH3:27])[CH3:26]>C(Cl)Cl>[CH2:24]([O:28][C:29]([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])[CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62365Isobutyl chloroformateHCID 27611434-(5-Piperidin-4-yl-1,2,4-oxadiazol-3-yl)pyridine

Product 1

HCID 11484315HCID 11484315, 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 isobutylchloroformate (54 mg, 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, evaporated and the residue purified by flash chromatography (IH-EtOAc, 1:1 to 0:1) to afford the title compound: RT=3.42 min, m/z (ES+)=331.2 [M+H]+.

Workup

  1. customthen quenched with saturated aqueous NaHCO3 (1 ml)
  2. customThe organic phase was separated
  3. customevaporated
  4. customthe residue purified by flash chromatography (IH-EtOAc, 1:1 to 0:1)

Sources & evidence

ORD record
ord-05bada90c5404bd48c13a8e4c03f6048
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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