HCID 14973730, compound → HCID 178437576, compound

HRID 541283Notes

Reaction equation

HRID 541283 reaction equation
[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][C:18]([CH2:20][CH3:21])=[N:17][N:16]=3)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:23][Si](CC=[N+]=[N-])(C)C>CO.ClCCl>[CH:1]1([C:5]2[C:14]([C:15]3[NH:19][CH:18]([CH2:20][CH3:21])[N:17]([CH3:23])[N:16]=3)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14973730HCID 14973730, compoundHCID 178437950HCID 178437950, compound2×

Product 1

HCID 178437576HCID 178437576, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-cyclobutyl-5-(5-ethyl-4H-1,2,4-triazol-3-yl)-2-methylbenzoate (compound 164.1, 87 mg, 0.29 mmol) was dissolved in methanol and dichloromethane (1:1 v/v) (6 ml). ((Trimethylsilyl)methyl)diazomethane (2.0 M in ether) (220 ul, 0.44 mmol) was added. The mixture was stiffed for 16 hours and quenched with HOAc (300 ul). The volatiles were removed in vacuo to afford an oil (85 mg). The residue was carried as crude onto the next step without further purification. m/z (ES+) 314 (M+H)+.

Workup

  1. customquenched with HOAc (300 ul)
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-33d5180c2ac64cf2b09214576618083f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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