Pyridine → HCID 10359927, compound

HRID 2252330Notes

Reaction equation

HRID 2252330 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.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl>[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][NH:17][C:28](=[O:30])[CH3:29])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 17974505HCID 17974505, compound

Product 1

HCID 10359927HCID 10359927, compoundYield 68%

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 (30 mg, 0.1 mmol) in dichloromethane (400 μL) was added pyridine (16 μL, 0.2 mmol) and acetic anhydride (9 μL, 0.1 mmol) and the reaction stirred for 25 minutes at ambient temperature. The reaction was concentrated in vacuo to an oily residue. The residue was purified by flash chromatography (eluting with 10% methanol/ethyl acetate), followed by trituration with diethyl ether to yield the title compound as a white solid (23 mg, 68%). MS (M+1)=341.4.

Workup

  1. concentrationThe reaction was concentrated in vacuo to an oily residue
  2. customThe residue was purified by flash chromatography (eluting with 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6145814b31f646fcafc72ce2a2815388
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

Loading…