Triethylamine → HCID 56595552, compound

HRID 1179247Notes

Reaction equation

HRID 1179247 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)OC1C=CC=CC=1)#[N:2].Cl.[NH:24]([C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1)[NH2:25].C(N(CC)CC)C>C(O)(C)C.CN(C)C1C=CN=CC=1>[NH2:2][C:1]1[N:24]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[N:25]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13473152HCID 13473152, compoundHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 56595552HCID 56595552, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolvent

Procedure

To N-cyano-N′-(3,4-dimethoxy-phenyl)-O-phenylisourea (0.215 g, 0.723 mmoles) in isopropanol (3 mL) was added 0.184 g (1.5 equivalents) of 4-Hydrazino-benzonitrile hydrochloride, followed by triethylamine 152 uL (1.5 equivalents) and catalytic (0.2 equivalents) 4-dimethylaminopyridine. The reaction was stirred overnight at 100 degrees Celsius. The reaction mixture was concentrated to dryness and purified by reverse phase column chromatography. The pure fractions were dried to provide 4-[5-amino-3-(3,4-dimethoxy-phenylamino)-[1,2,4]triazol-1-yl]-benzonitrile as tan solid (18.3 mg, 7.5% yield).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by reverse phase column chromatography
  3. customThe pure fractions were dried

Sources & evidence

ORD record
ord-ea240c5147964c81a03acb66e8970830
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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