2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide → HCID 178458212, compound

HRID 1925131Notes

Reaction equation

HRID 1925131 reaction equation
[OH:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][NH:12][C:13](=[S:24])NC2C=CC([N+]([O-])=O)=CC=2)=[N:9][CH:10]=1)([CH3:4])[CH3:3]>COCCOC>[SH:24][C:13]1[N:9]2[CH:10]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[CH:6]=[CH:7][C:8]2=[N:11][N:12]=1

Participants

3

Reactant 1

HCID 866398192-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide

Product 1

HCID 178458212HCID 178458212, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-(6-hydrazinylpyridin-3-yl)propan-2-ol (250 mg, 1.495 mmol) and 1-isothiocyanato-4-nitrobenzene (269 mg, 1.495 mmol) in ACN (Volume: 2.0 mL) was stirred at room temperature for 1 hr. The reaction was diluted with Et2O (Volume: 5.0 mL), and the resulting solid was filtered. Minimal product was present in the solid. On standing for 1 hr, the filtrate had formed a precipitate. This was filtered to provide 2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide (175 mg, 0.504 mmol, 33.7% yield) as an orange solid. A solution of 2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide (275 mg, 0.792 mmol) in DME (Volume: 2.0 mL) was heated in a microwave on high absorbance for 3 hr at 110° C. The reaction was stripped to dryness onto silica gel via rotary evaporation and purified compound by MPLC with DCM:MeOH (98:2) to provide 2-(3-mercapto-[1,2,4]triazolo[4,3-a]pyridin-6-yl)propan-2-ol.

Workup

  1. customThe reaction was stripped to dryness onto silica gel via rotary evaporation
  2. custompurified compound by MPLC with DCM:MeOH (98:2)

Sources & evidence

ORD record
ord-5869bc5e1b0f4a079dcf8c3b8e78ea31
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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