Bicarbonate Ion → 5-Methyl-2-(5-phenyl-2H-1,2,4-triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1627736Notes

Reaction equation

HRID 1627736 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10]1[N:19]=[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[N:12]2[N:11]=1.CN(C)C=O.[C:25]1([C:31]2[N:32]=[C:33]([SH:36])[NH:34][N:35]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-]>CCOC(C)=O>[CH3:18][C:17]1[N:12]2[N:11]=[C:10]([CH2:9][S:36][C:33]3[NH:34][N:35]=[C:31]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:32]=3)[N:19]=[C:13]2[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 769Bicarbonate IonHCID 6228DimethylformamideHCID 8471TriethylamineHCID 672565572-(Chloromethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyridineHCID 178418866HCID 178418866, compound

Product 1

HCID 1784239795-Methyl-2-(5-phenyl-2H-1,2,4-triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (0.7602 mL, 5.454 mmol) was added to a solution of [2-Chloromethyl-5-methyl-(1,2,4]triazolo[1,5-a]pyridine (495 mg, 2.73 mmol) in N,N-Dimethylformamide (12 mL, 150 mmol) and the solution was stirred aprox 2 mins. 5-Phenyl-2H-1,2,4-triazole-3-thiol (532 mg, 3.00 mmol) was added to the mixture as a solid. The reaction mixture was subsequently heated at 60° C. for 0.5 hours. The mixture was rotovaped. EtOAc (60 mL) and sat. bicarbonate (20 mL) were added to the residue and the phases were separated. The organic phase was washed with brine (20 mL). After drying (MgSO4), the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (Eluent: EtOAC:N-heptane 50-100%). This afforded 542 mg (61%) of the title compound as a white solid. LC-MS: m/z=323.1 (MH+), tR=0.52 min, Method B. 1H NMR (600 MHz, DMSO-ds): δ 7.96 (d, 2H), 7.63 (m, 1H), 7.60 (t, 1H) 7.50 (m, 3H), 7.06 (d, 1H), 4.68 (s, 2H), 2.67 (s, 3H).

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine (20 mL)
  3. dry with materialAfter drying (MgSO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by silica gel chromatography (Eluent: EtOAC:N-heptane 50-100%)

Sources & evidence

ORD record
ord-73f69b37e41a43b7941134706107a4c4
Source dataset
uspto-grants-2014_07
Patent number
US08785653B2

Reaction notes

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