1-Hydroxybenzotriazole → HCID 68507277, compound

HRID 1715307Notes

Reaction equation

HRID 1715307 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[O:4].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O[NH:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[C:48]([C:58]([F:61])([F:60])[F:59])[CH:47]=1)=[NH:45]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([C:15]2[O:17][N:45]=[C:44]([C:46]3[CH:51]=[CH:50][C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[C:48]([C:58]([F:59])([F:60])[F:61])[CH:47]=3)[N:43]=2)=[CH:18][CH:19]=1)(=[O:9])=[O:10]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43219016HCID 43219016, compoundHCID 178513263HCID 178513263, compound

Product 1

HCID 68507277HCID 68507277, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Methoxycarbonyl-ethylsulfamoyl)-benzoic acid (1 eq) is dissolved in DMF 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 90° C. 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/CH2Cl2 8/2/1 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-4ad94e4ccc894b2da01a27e805ad84b7
Source dataset
uspto-grants-2010_09
Patent number
US07799812B2

Reaction notes

Loading…