Azidotrimethylsilane → HCID 178464871, compound

HRID 1717417Notes

Reaction equation

HRID 1717417 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)[N:9]=[N:8][C:7]=1[C:22]([NH:24][CH:25]1[CH2:27][CH2:26]1)=[O:23])#[N:2].C[Si]([N:32]=[N+:33]=[N-:34])(C)C>C1(C)C=CC=CC=1>[CH:25]1([NH:24][C:22]([C:7]2[N:8]=[N:9][N:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:16]=3)[C:6]=2[CH2:5][CH2:4][CH2:3][C:1]2[NH:34][N:33]=[N:32][N:2]=2)=[O:23])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 57665055HCID 57665055, compound

Product 1

HCID 178464871HCID 178464871, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(3-cyanopropyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (183 mg, 0.5 mmol) obtained in Example 1207, trimethylsilyl azide (58 mg, 0.5 mmol) and di-N-butyltin oxide (12.5 mg, 0.05 mmol) in toluene (5 ml) was boiled under reflux for 24 hr and the solvent was evaporated. Methanol (5 ml) was added to the residue, and the solvent was evaporated again. Ethyl acetate (10 ml) and 6% aqueous sodium bicarbonate solution (10 ml) were added to the residue and, after partitioning, the aqueous layer was adjusted to pH 4-5 with 1N hydrochloric acid, and the precipitated crystals were collected by filtration and dried to give the title compound as a colorless powder (55 mg, 27%).

Workup

  1. temperatureunder reflux for 24 hr
  2. customthe solvent was evaporated
  3. additionMethanol (5 ml) was added to the residue
  4. customthe solvent was evaporated again
  5. additionEthyl acetate (10 ml) and 6% aqueous sodium bicarbonate solution (10 ml) were added to the residue
  6. customafter partitioning
  7. filtrationthe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-cc4a927e81cc4d0db3eead5db11ef3b1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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