Hydrochloric Acid → HCID 58574175, compound

HRID 1619310Notes

Reaction equation

HRID 1619310 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[N:15]4[CH2:23][C:22]5(OCC[O:24]5)[CH2:21][CH2:20][C:16]4=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[N:15]4[CH2:23][C:22](=[O:24])[CH2:21][CH2:20][C:16]4=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58574182HCID 58574182, compound

Product 1

HCID 58574175HCID 58574175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3′-((3-fluorophenyl)ethynyl)-6′,7′-dihydrospiro[[1,3]dioxolane-2,8′-pyrido[2,1-b]quinazolin]-11′(9′H)-one (0.5 g, 1.3 mmol) and 4N HCl (4 mL) in THF (20 mL) was heated at reflux for 4 h. After it was cooled to room temperature, the reaction mixture was quenched with Na2CO3 solution and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 333 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.28-8.25 (d, J=8.19 Hz, 1H), 7.82 (s, 1H), 7.63-7.60 (dd, J=8.22, 1.50 Hz, 1H), 7.39-7.35 (m, 2H), 7.28-7.27 (m, 1H), 7.15-7.09 (m, 1H), 4.28 (s, 2H), 3.34-3.30 (t, 2H), 2.85-2.81 (t, 2H). mGluR5 PAM EC50: +++. Fold shift at 10 μM: +.

Workup

  1. temperatureat reflux for 4 h
  2. customthe reaction mixture was quenched with Na2CO3 solution
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8e2a5f867fef464eb043f2b1f70c5fe9
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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