Trifluoroacetic acid → HCID 67959631, compound

HRID 1529415Notes

Reaction equation

HRID 1529415 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[N:20]=[C:19]([O:21][C@H:22]2[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26][C:23]32[CH2:25][CH2:24]3)[CH:18]=[N:17][CH:16]=1)([CH3:5])C.[C:37](O)(C(F)(F)F)=O>CO.C(Cl)Cl>[CH2:25]1[C:23]2([CH2:26][CH2:27][NH:28][CH2:29][C@@H:22]2[O:21][C:19]2[N:20]=[C:15]([C:9]3[C:8]4[C:12](=[CH:13][CH:14]=[C:6]([CH:3]([CH3:5])[CH2:2][OH:1])[CH:7]=4)[N:11]([CH3:37])[N:10]=3)[CH:16]=[N:17][CH:18]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67960052HCID 67960052, compound

Product 1

HCID 67959631HCID 67959631, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of (R)-tert-butyl 4-((6-(5-(1-hydroxy-2-methylpropan-2-yl)-1H-indazol-3-yl)pyrazin-2-yl)oxy)-6-azaspiro[2.5]octane-6-carboxylate (18 mg, 0.036 mmol) in TFA (41.6 mg, 0.365 mmol) was stirred at RT for 30 min. The mixture was concentrated and was dissolved in MeOH (˜20 mg/ml) and injected (1×1.000 ml) onto the Shimadzu preparatory LC (Protocol B) before the pure fraction was concentrated via rotary evaporation to give impure product. A preparatory TLC plate was loaded with the crude mixture and run 2 times in 20% MeOH/DCM; scraping the plate, extraction with MeOH, filtration, and concentration via rotary evaporation afforded 2-(3-(6-((4R)-6-azaspiro[2.5]oct-4-yloxy)-2-pyrazinyl)-1-methyl-1H-indazol-5-yl)-1-propanol (7.6 mg, 0.019 mmol, 53.0% yield) as a beige solid. MS (ESI, pos. ion) m/z: 394.0 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionwas dissolved in MeOH (˜20 mg/ml)
  3. concentrationwas concentrated via rotary evaporation
  4. customto give impure product
  5. extractionthe plate, extraction
  6. filtrationwith MeOH, filtration, and concentration
  7. customvia rotary evaporation

Sources & evidence

ORD record
ord-f835be8c2e90473e818ea6652c679413
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…