Triethylamine → HCID 69938070, compound

HRID 1619422Notes

Reaction equation

HRID 1619422 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CCN(CC)CC.[NH2:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:35])[N:24]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:25]3=[N:26]2)=[CH:21][CH:20]=1>O=S(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23](=[O:35])[N:24]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:25]4=[N:26]3)=[CH:21][CH:20]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 99734-Fluorobenzoic AcidHCID 58574405HCID 58574405, compound

Product 1

HCID 69938070HCID 69938070, compoundYield 6.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 4-fluorobenzoic acid (100 mg, 0.71 mmol) in SOCl2 (2 mL) was stirred at reflux for 1 h. Excess SOCl2 was removed and the residue was dissolved in THF (10 mL). The solution was added to a mixture of Et3N (1 mL) and 3-amino-8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-one (22 mg, 0.09 mmol). After stirring for 1 h, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (2 mg). MS (ESI): 366 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=8.70 Hz, 1H), 7.96-7.91 (m, 4H), 7.75-7.71 (dd, J=8.72 Hz, 2.12 Hz, 1H), 7.24-7.19 (t, J=8.60 Hz, 2H), 4.34 (broad, 2H), 3.06-3.02 (m, 2H), 1.99-1.87 (m, 4H), 1.68-1.66 (m, 2H), 1.47-1.46 (d, J=4.32 Hz, 2H). mGluR5 PAM EC50: +.

Workup

  1. temperatureat reflux for 1 h
  2. customExcess SOCl2 was removed
  3. dissolutionthe residue was dissolved in THF (10 mL)
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6493774d8e01418bbe60a799cbd1d8b2
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…