Hydrochloric Acid → HCID 178479609, compound

HRID 1754554Notes

Reaction equation

HRID 1754554 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[N:26](COCC[Si](C)(C)C)[N:25]=[CH:24][C:13]=4[C:14](=[O:23])[N:15]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:16]=3[CH:17]=2)[CH:2]=1.FC(F)(F)CN1C2C3C=CC=CC=3NC(=O)C=2CN1COCC[Si](C)(C)C.[ClH:62]>O1CCOCC1>[ClH:62].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[C:13](=[CH:24][NH:25][N:26]=4)[C:14](=[O:23])[N:15]([CH2:18][C:19]([F:20])([F:21])[F:22])[C:16]=3[CH:17]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 86679793HCID 86679793, compoundHCID 86679794HCID 86679794, compound

Product 1

HCID 178479609HCID 178479609, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 7-(pyrid-3-yloxy)-5-(2,2,2-trifluoroethyl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one and (2,2,2-trifluoroethyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (0.19 g, 0.39 mmol) in 10 mL of anhydrous hydrogen chloride dissolved in dioxane (4M) is stirred at room temperature for 18 hours. The suspension is filtered and the solid is washed with DCM and then purified by flash chromatography on a C18 reverse phase (H2O/MeCN: 100/0 to 0/100). The gum obtained is dissolved in molar hydrochloric acid solution and then concentrated to dryness to give 78 mg of a white powder (1.2 hydrochloride, 1.15 H2O; yield: 58%).

Workup

  1. filtrationThe suspension is filtered
  2. washthe solid is washed with DCM
  3. custompurified by flash chromatography on a C18 reverse phase (H2O/MeCN: 100/0 to 0/100)
  4. customThe gum obtained
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8f455b6e6c06497b8ed8be455d335682
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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