Triethylamine → HCID 69519305, compound

HRID 1179939Notes

Reaction equation

HRID 1179939 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.C(NC1C=CC([O:27][C:28]([N:30]2[CH2:35][CH2:34][CH:33]([O:36][Si](C(C)(C)C)(C)C)[CH2:32][CH2:31]2)=O)=NC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.F>C(#N)C.CCCCCCC>[F:10][C:8]([F:9])([F:11])[C:5]1[CH:6]=[CH:7][C:2]([O:1][C:28]([N:30]2[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]2)=[O:27])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14917Hydrofluoric AcidHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterHCID 178516044HCID 178516044, compound

Product 1

HCID 69519305HCID 69519305, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8900HeptaneSolvent

Procedure

A solution of 2-hydroxy-5-trifluoromethylpyridine (0.32 g, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in acetonitrile (10 mL) was stirred at room temperature for three days. Hydrofluoric acid (min. 40% in water, 0.50 mL) was added and stirring was continued for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 75:25), followed by crystallisation from ethyl-acetate:heptane, yielding the title compound (0.27 g, 47% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 75:25)
  3. customfollowed by crystallisation from ethyl-acetate

Sources & evidence

ORD record
ord-8290ad4ec25449beb33de472e2be1740
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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