Trimethylsilyldiazomethane → HCID 58964480, compound

HRID 2069263Notes

Reaction equation

HRID 2069263 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[C:11]([N:18]2[CH:22]=[N:21][N:20]=[CH:19]2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH3:23][Si](C=[N+]=[N-])(C)C>CO.CCCCCC>[CH3:23][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([N:18]2[CH:22]=[N:21][N:20]=[CH:19]2)[C:12]([C:14]([F:17])([F:15])[F:16])=[CH:13][C:5]=1[NH:4][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 58964520HCID 58964520, compound

Product 1

HCID 58964480HCID 58964480, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent2×

Procedure

A solution of 1.3 g (4.14 mmol) of 2-acetylamino-5-[1,2,4]triazol-4-yl-4-trifluoromethyl-benzoic acid in 15 ml of methanol is treated dropwise with 3.1 ml (6.21 mmol) of a 2M solution of trimethylsilyl diazomethane in hexane. The mixture is stirred for 1 hour at room temperature and another 1.5 ml (3.00 mmol) of a solution of trimethylsilyl diazomethane in hexane (2M) is added. After 1 hour, the reaction is quenched by adding glacial acetic acid until no more gas evolution is observed. The mixture is concentrated in vacuo and the residue taken up in ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, gradient 100% ethyl acetate to ethyl acetate/methanol 9:1) afforded 456 mg (34%) of 2-acetylamino-5-[1,2,4]triazol-4-yl-4-trifluoromethyl-benzoic acid methyl ester as yellow crystals, m.p. 180-184° C.

Workup

  1. waitAfter 1 hour
  2. customthe reaction is quenched
  3. additionby adding glacial acetic acid until no more gas evolution
  4. concentrationThe mixture is concentrated in vacuo
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (SiO2, gradient 100% ethyl acetate to ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-e5279ec7766f433e9ff2318a0b240711
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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