Hydrochloric Acid → HCID 86601248, compound

HRID 2251982Notes

Reaction equation

HRID 2251982 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH2:18]O)[N:9]=[N:8]1.Cl.Cl.[OH:31][NH2:32].O>CS(C)=O>[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH:18]=[N:32][OH:31])[N:9]=[N:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 86601206HCID 86601206, compound

Product 1

HCID 86601248HCID 86601248, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add 3 eq sulfur trioxide pyridine complex (Aldrich) to a solution of [1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazol-4-yl]-methanol in DMSO, then add 10 eq TEA. Stir for 6 hours, pour into 15 ml 1N HCl and extract with EtOAc (2×20 ml). Remove solvent and dissolve the crude aldehyde in MeOH. Add 1.5 eq of hydroxyl amine hydrochloride and stir for 6 hours. Pour into 50 ml water and extract with EtOAc. Purify via radial chromatography 1:1 hexanes:EtOAc to give the title compound. MS (IS) 416.1 (M+1). Rf=0.16 (1:1 hexanes:EtOAc).

Workup

  1. extractionextract with EtOAc (2×20 ml)
  2. dissolutionRemove solvent and dissolve the crude aldehyde in MeOH
  3. stirringstir for 6 hours
  4. extractionextract with EtOAc
  5. customPurify via radial chromatography 1:1 hexanes

Sources & evidence

ORD record
ord-e0c9e90068814da2b98e5f2a5594fdff
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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