N,N-Diethylethanamine trihydrofluoride → HCID 58042365, compound

HRID 2048063Notes

Reaction equation

HRID 2048063 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([CH3:20])[CH3:19])[N:13]=[CH:12]2)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C>CO>[CH:18]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[N:13]1)([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 58042438HCID 58042438, compound

Product 1

HCID 58042365HCID 58042365, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-{[tert-Butyl(dimethyl)silyl]oxy}-1-isopropyl-1H-indazole (Preparation 40, 238 mg, 0.819 mmol), triethylamine trishydrofluoride (132 mg, 0.819 mmol) and methanol were combined and stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was concentrated in vacuo and the residue redissolved with methanolic ammonia and again concentrated in vacuo. The procedure was repeated once more and the residue purified by silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound (123 mg, 86%):

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue redissolved with methanolic ammonia
  3. concentrationagain concentrated in vacuo
  4. customthe residue purified by silica gel chromatography
  5. washeluting with 0 to 30% EtOAc in heptane

Sources & evidence

ORD record
ord-b7734791cce24d32a67a420deeaeec22
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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