Hydrochloric Acid → HCID 58574874, compound

HRID 1619355Notes

Reaction equation

HRID 1619355 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[CH2:24][CH2:23]/[C:22](=[CH:25]\[O:26]C)/[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[CH2:24][CH2:23][CH:22]([CH:25]=[O:26])[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 58574510HCID 58574510, compound

Product 1

HCID 58574874HCID 58574874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (Z)-3-((3-fluorophenyl)ethynyl)-8-(methoxymethylene)-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one (0.1 g, 0.8 mmol, 1 equiv) and 4N HCl (4 mL) in THF (20 mL) was heated at reflux for 4 h. After it was cooled to rt, the reaction mixture was quenched with Na2CO3 aqueous 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): 361 (MH+).

Workup

  1. temperatureat reflux for 4 h
  2. customthe reaction mixture was quenched with Na2CO3 aqueous
  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-0e61bfb26430455597938e3b94c8eb2b
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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