Tripropylamine → HCID 135844949, compound

HRID 707456Notes

Reaction equation

HRID 707456 reaction equation
[CH:1]([NH:3][NH2:4])=[O:2].C([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9]CC)CC.C(C1C=[CH:20][S:19][C:18]=1[NH:22]C(=O)OC)#N>COCCO>[N:8]1[CH:9]=[N:4][N:3]2[C:12]=1[C:13]1[CH:14]=[CH:20][S:19][C:18]=1[NH:22][C:1]2=[O:2]

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 12229HydrazinecarboxaldehydeHCID 14015027HCID 14015027, compound

Product 1

HCID 135844949HCID 135844949, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Formylhydrazine (2.08 g, 34.6 mmol) and tri-n-propylamine (3 mL) was added to a suspension of methyl 3-cyanothiophen-2-ylcarbamate (6 g, 32.9 mmol) in 2-methoxyethanol (70 mL) at room temperature. The mixture was heated at reflux overnight under nitrogen. The mixture was concentrated under vacuum to give a crude product, which was purified by preparative HPLC to give 1.8 g (26%) of thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one as a solid. 1H NMR (400 MHz, DMSO) δ 7.28-7.30 (d, 1H), 7.39-7.41 (d, 1H), 8.34 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight under nitrogen
  3. concentrationThe mixture was concentrated under vacuum
  4. customto give a crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-6c7a2769ef1840279370135a6c190431
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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