1-Hydroxybenzotriazole → HCID 57709590, compound

HRID 1715308Notes

Reaction equation

HRID 1715308 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O[NH:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:42]([C:52]([F:55])([F:54])[F:53])[CH:41]=1)=[NH:39]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]([C:5]2[O:7][N:39]=[C:38]([C:40]3[CH:45]=[CH:44][C:43]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[C:42]([C:52]([F:53])([F:54])[F:55])[CH:41]=3)[N:37]=2)=[CH:8][CH:9]=[C:10]([O:12][CH3:13])[N:11]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8531782,6-Dimethoxypyridine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178513263HCID 178513263, compound

Product 1

HCID 57709590HCID 57709590, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Dimethoxy-nicotinic acid (1 eq) is dissolved in dioxane and EDC.HCl (1.3 eq) and HOBt (1.1 eq) are added. After 30 minutes at room temperature N-hydroxy-2-trifluoromethyl-biphenyl-4-carboxamidine (1 eq) is added and the reaction mixture is kept at 900 degrees Celsius for 16 hours. After removal of the solvent the residue is dissolved in ethyl acetate and extracted with saturated NaHCO3 solution. Title compound is obtained after drying of the organic phase over Na2SO4 on silica gel using c-hexane/ethyl acetate→c-hexane/ethyl acetate 100→70/30 as mobile phase.

Workup

  1. customAfter removal of the solvent the residue
  2. dissolutionis dissolved in ethyl acetate
  3. extractionextracted with saturated NaHCO3 solution

Sources & evidence

ORD record
ord-fc67ceedfe0a401a936b01f3993990af
Source dataset
uspto-grants-2010_09
Patent number
US07799812B2

Reaction notes

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