Methyl iodide → HCID 58081314, compound

HRID 928357Notes

Reaction equation

[CH2:1]([O:5][C:6]([C:8]1[N:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:10][N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[C:20](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:12]=[C:11]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:10]([CH3:20])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 23 °C

Procedure

5-Benzyl-1H-[1,2,4]triazole-3-carboxylic acid butyl ester (100 mg, 0.386 mmol) was dissolved in acetone (3 ml), to which were added potassium carbonate (80 mg, 0.578 mmol) and iodomethane (27 μl, 0.432 mmol) as a solution in acetone (2 ml) at 23° C. The reaction mixture was stirred at 23° C. for 72 h, then filtered and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate; 25 g column; flow 40 ml/min; 0% ethyl acetate to 100% ethyl acetate in 20 min) to give the title compound. UPLC-MS (method F) Rt=0.96 min, [M+H]+=274.3.

Workup

filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate; 25 g column; flow 40 ml/min; 0% ethyl acetate to 100% ethyl acetate in 20 min)

Sources & evidence

ORD record: ord-4009f9e9e4c7419a8e9487d694016172
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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