Triethylamine → HCID 178509309, compound

HRID 82706Notes

Reaction equation

HRID 82706 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH2:9][C:10]1[C:11]([C:15](Cl)=[N:16][OH:17])=[N:12][O:13][N:14]=1.C(N(CC)CC)C>C(O)C>[NH2:9][C:10]1[C:11]([C:15](=[N:16][OH:17])[NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=2)=[N:12][O:13][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97423-FluoroanilineHCID 4040027(Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chloride

Product 1

HCID 178509309HCID 178509309, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3-fluoroaniline (36 μL, 0.37 mmol) in ethanol (0.5 mL) was treated with a solution of 4-amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (50 mg, 0.31 mmol) in ethanol (1.5 mL) followed by triethylamine (51 μL, 0.37 mmol) dropwise. The reaction mixture was stirred at 25° C. for 1 h and purified by preparative LCMS to give the desired product (21 mg, 29%). LCMS for C9H9FN5O2 (M+H)+: m/z=238.0.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-3c8140e7211443c48fb50c8d2a396280
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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