Triethylamine → HCID 23158187, compound

HRID 601677Notes

Reaction equation

HRID 601677 reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([CH2:6][N:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:16]4[N:17]=[N:18][N:19]([C:22]5[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=5)[C:20]=4[CH3:21])[CH:13]=3)[C:8]2=[O:29])[CH2:3]1.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:6][N:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:16]4[N:17]=[N:18][N:19]([C:22]5[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=5)[C:20]=4[CH3:21])[CH:13]=3)[C:8]2=[O:29])[CH2:5]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 23158143HCID 23158143, compound

Product 1

HCID 23158187HCID 23158187, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 mg of 4-[2-(3-hydroxy-cyclobutylmethyl)-1-oxo-isoindoline-5-yl]-1-(2-fluoropyridine-3-yl)-5-methyl-1H-[1,2,3]triazole obtained in Example 132 was dissolved in 1 ml of dimethylsulfoxide, and 100 μl of triethylamine followed by 40 mg of sulfur trioxide/pyridine complex were added at room temperature and the mixture was stirred for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were purified by preparative thin-layer silicagel chromatography (chloroform:methanol=20:1) to obtain 12 mg of the above compound as a white solid.

Workup

  1. additionwere added at room temperature
  2. washwashed with water and saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvents were distilled outunder reduced pressure
  5. customthe residues were purified by preparative thin-layer silicagel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-97aff915a54b4fa384e4275c540e40f3
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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