Sulfuric Acid → HCID 58574122, compound

HRID 1619411Notes

Reaction equation

HRID 1619411 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=[O:24])[N:14]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:15]4=[N:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:25]S(O)(=O)=O>>[C:1]1([CH2:7][C:8]([C:9]2[CH:18]=[C:17]3[C:12]([C:13](=[O:24])[N:14]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:15]4=[N:16]3)=[CH:11][CH:10]=2)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 53252176HCID 53252176, compound

Product 1

HCID 58574122HCID 58574122, compound

Procedure

A mixture of 3-(phenylethynyl)-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one (400 mg, 1.3 mmol), HgSO4 (0.1 g, 0.3 mmol, 0.2 equiv) and H2SO4 (6 mL) was stirred at room temperature for 2 h. After quenching with water and basifying with saturated sodium carbonate, the solution was extracted with ethyl acetate (3×20 mL). The combined organic layers were concentrated. The residue was purified by silica gel chromatography to give the desired product (30 mg). MS (ESI): 333 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.22-8.19 (d, J=8.16 Hz, 1H), 8.03-7.99 (d, J=7.14 Hz, 2H), 7.59-7.43 (m, 4H), 7.37-7.34 (d, J=8.19 Hz, 1H), 4.40 (s, 2H), 4.39-4.36 (t, J=5.34 Hz, 2H), 3.06-3.03 (t, J=3.60 Hz, 2H), 1.85-1.81 (m, 6H). mGluR5 PAM EC50: ++.

Workup

  1. customAfter quenching with water and basifying with saturated sodium carbonate
  2. extractionthe solution was extracted with ethyl acetate (3×20 mL)
  3. concentrationThe combined organic layers were concentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e0e512c6d3e4cc59be8428b238974f2
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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