HCID 68872676, compound → HCID 135984674, compound

HRID 2374935Notes

Reaction equation

HRID 2374935 reaction equation
O=[C:2]([CH:8]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH3:9])[C:3](OCC)=[O:4].C(=O)(O)O.[NH2:27][NH:28][C:29]([NH2:31])=[NH:30]>CCO>[NH2:30][C:29]1[NH:31][C:3](=[O:4])[C:2]([CH:8]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH3:9])=[N:27][N:28]=1

Participants

4

Reactant 2

HCID 68872676HCID 68872676, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 135984674HCID 135984674, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-oxo-3-{[3-(trifluoromethyl)benzoyl]amino}butanoate (8.75 g, 27.6 mmol) and aminoguanidine bicarbonate (3.75 g, 27.6 mmol) in EtOH(aq) (80%, 200 mL) was heated at reflux for 3h. Concentration gave crude N-[1-(3-amino-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)ethyl]-3-(trifluoromethyl)benzamide (8.34 g) as a colourless solid which was used without further purification. 1H NMR (DMSO-d6): δ8.87 (d, J=7.5 Hz, 1H), 8.23 (s, 1H), 8.20-8.15 (m, 2H), 7.93-7.89 (m, 1H), 7.75-7.69 (m, 1H), 7.00 (bs, 1H), 5.16 (p, J=7.1 Hz, 1H), 1.40 (d, J=7.1 Hz, 3H). MS m/z 326 (M−1).

Workup

  1. temperatureat reflux for 3h
  2. concentrationConcentration

Sources & evidence

ORD record
ord-d803ca7c09e646c49cfed600d979eece
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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