HCID 58574313, compound → HCID 58574547, compound

HRID 1619363Notes

Reaction equation

HRID 1619363 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]3[C:14](=[O:25])[N:15]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C:16]4=[N:17][C:18]=3[CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[O:26]1[CH2:30][CH2:29][CH:28](OS(C2C=CC=CC=2)(=O)=O)[CH2:27]1>C(#N)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]3[C:14](=[O:25])[N:15]4[CH2:24][CH2:23][N:22]([CH:28]5[CH2:29][CH2:30][O:26][CH2:27]5)[CH2:21][CH2:20][C:16]4=[N:17][C:18]=3[CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 58574313HCID 58574313, compoundHCID 58574684HCID 58574684, compound

Product 1

HCID 58574547HCID 58574547, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 8-((3-fluorophenyl)ethynyl)-2,3,4,5-tetrahydro-[1,4]diazepino[7,1-b]quinazolin-11(1H)-one (100 mg, 0.3 mmol) and tetrahydrofuran-3-yl-benzenesulfonate (137 mg, 0.6 mmol) in acetonitrile (20 mL) was stirred at room temperature overnight. The mixture was diluted with H2O (50 mL) and extracted with ethyl acetate (3×50 mL), the combined organic layers were washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI):404 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.25-8.22 (d, J=8.25 Hz, 1H), 7.77 (s, 1H), 7.58-7.55 (dd, J=8.25, 1.38 Hz, 1H), 7.40-7.34 (m, 2H), 7.28-7.26 (m, 1H), 7.13-7.06 (m, 1H), 4.61-4.32 (m, 2H), 4.02-3.95 (m, 1H), 3.90-3.70 (m, 3H), 3.25-3.22 (m, 3H), 2.89-2.74 (m, 4H), 2.09-1.86 (m, 2H). mGluR5 PAM EC50: ++.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-05933856b8574d70af519b0c0b680739
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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