Dibutyltin oxide → HCID 178492208, compound

HRID 1179256Notes

Reaction equation

HRID 1179256 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[N:3]=1.C[Si]([N:30]=[N+:31]=[N-:32])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:25][O:24][C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=1[NH:15][C:4]1[N:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:8]=[CH:9][C:10]([C:11]3[NH:32][N:31]=[N:30][N:12]=3)=[CH:13][CH:14]=2)[N:5]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 58976948HCID 58976948, compound

Product 1

HCID 178492208HCID 178492208, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-[5-Amino-3-(2,4-dimethoxy-phenylamino)-[1,2,4]triazol-1-yl]-benzonitrile (52 mg, 0.15 mmol) and trimethylsilyl azide (20 mg, 0.165 mol) were suspended in 1 mL toluene with a catalytic amount of di-butyltin oxide and heated to 110° C. for 18 hours. The toluene was evaporated and the residue purified by preparative HPLC affording 13 mg product as the TFA salt.

Workup

  1. customThe toluene was evaporated
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-fd4616993e8f4acaa90bd2f3e56f183a
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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