Hydrochloric Acid → 1-Hydroxybenzotriazole

HRID 1370583Notes

Reaction equation

HRID 1370583 reaction equation
[CH3:1][NH2:2].Cl.CC[N:6](C(C)C)C(C)C.CN(C)CCCN=C=NCC.[NH2:24][C:25]1[C:30](/C=C/C(O)=O)=[CH:29][C:28](Cl)=[CH:27]N=1.C(C(O)=O)(F)(F)F.[OH2:44]>CN(C=O)C.C(OCC)C>[OH:44][N:2]1[C:1]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[N:6]1

Participants

10

Reactant 7

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 6329MethylamineHCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 18752895HCID 18752895, compound

Product 1

HCID 757711-Hydroxybenzotriazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

H2O (196 mg, 1.4 mmol), methylamine.HCl (114 mg, 1.7 mmol), Hunig's base (1.58 ml, 9.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (555 mg, 2.8 mmol) and (E)-3-(2-amino-5-chloro-3-pyridinyl)-2-propenoic acid.CF3CO2H (438 mg, 1.4 mmol) were combined in DMF (5 ml) and stirred at RT for 16 h. The reaction mixture was poured into water (50 ml), extracted with EtOAc (3×20 ml), and the combined organic extracts washed with saturated brine, dried over MgSO4, and concentrated to a yellow solid. Trituration with diethyl ether gave the title compound (198 mg, 0.9 mmol).

Workup

  1. extractionextracted with EtOAc (3×20 ml)
  2. washthe combined organic extracts washed with saturated brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-f341e9e6869c40559e634df86ac2a285
Source dataset
uspto-grants-2003_06
Patent number
US06583162B1

Reaction notes

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