Acetone → HCID 67481493, compound

HRID 472489Notes

Reaction equation

HRID 472489 reaction equation
[NH2:1][C:2]1[N:11]=[C:5]2[C:6]([OH:10])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)=O.Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32]>>[NH2:1][C:2]1[N:11]=[C:5]2[C:6]([O:10][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 67478774N-(2-Bromomethyl-phenyl)-N-methyl-methanesulfonamideHCID 67481450HCID 67481450, compound

Product 1

HCID 67481493HCID 67481493, compound

Procedure

195 e) To a suspension of 2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-ol (0.20 g, 1.3 mmol) and cesium carbonate (0.47 g, 1.4 mmol) in dry acetone (5 mL, 70 mmol) was added N-(2-bromomethyl-phenyl)-N-methyl-methanesulfonamide (0.40 g, 1.4 mmol). The mixture was stirred for 2 hours at room temperature then heated at 40° C. for 18 hours. The mixture was cooled to room temperature and the volatiles were evaporated. The residue was triturated with water (30 mL). The water was decanted and the waxy solid was dissolved in dichloromethane (30 mL) and washed with water. The organic layer was dried over magnesium sulfate, filtered and evaporated. The recovered material was purified via chromatography (silica gel column 40 g and 0%→10% methanol:dichloromethane). N-[2-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl)-phenyl]-N-methyl-methanesulfonamide was isolated as an orange viscous oil (0.129 g, 28%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.96 (d, J=6.7 Hz, 1H), 7.73-7.68 (m, 1H), 7.40-7.28 (m, 3H), 6.88 (d, J=7.8 Hz, 1H), 6.71 (t, J=7.1 Hz, 1H), 5.48 (br s, 2H), 4.44 (s, 2H), 3.31 (s, 3H), 2.99 (s, 3H).

Workup

  1. temperaturethen heated at 40° C. for 18 hours
  2. temperatureThe mixture was cooled to room temperature
  3. customthe volatiles were evaporated
  4. customThe residue was triturated with water (30 mL)
  5. customThe water was decanted
  6. dissolutionthe waxy solid was dissolved in dichloromethane (30 mL)
  7. washwashed with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe recovered material was purified via chromatography (silica gel column 40 g and 0%→10% methanol:dichloromethane)

Sources & evidence

ORD record
ord-d96b7d1374d04b9c8055331b36a68265
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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