Pyridine → HCID 69205067, compound

HRID 2252328Notes

Reaction equation

HRID 2252328 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([S:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[CH2:16][NH2:17])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>ClCCl>[C:32]1([O:31][C:29](=[O:30])[NH:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13][C:10]2[CH:11]=[CH:12][C:7]3[N:8]([C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]=3)[CH:9]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 17974505HCID 17974505, compound

Product 1

HCID 69205067HCID 69205067, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-Isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-benzylamine (417 mg, 1.4 mmol) in dichloromethane (14 mL) at ambient temperature under nitrogen was added pyridine (226 μL, 2.8 mmol) and phenyl chloroformate (192 μL, 1.5 mmol). The reaction was stirred for 20 minutes, then quenched with saturated NaHCO3. The reaction mixture was extracted with dichloromethane, the combined organics washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography (eluting with ethyl acetate), followed by ether/hexane trituration gave the above named compound as a white solid (526 mg, 90%).

Workup

  1. customquenched with saturated NaHCO3
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washthe combined organics washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washby flash chromatography (eluting with ethyl acetate)
  8. customgave the

Sources & evidence

ORD record
ord-2b0ae2b1bef144938774c751a39659d4
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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