Methyl formate → HCID 58574552, compound

HRID 1619364Notes

Reaction equation

HRID 1619364 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.[CH:26](OC)=[O:27].N1CCCN2CCCN=C12>C1(C)C=CC=CC=1>[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:26]=[O:27])[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 3

HCID 7865Methyl formateHCID 79873TriazabicyclodeceneHCID 58574313HCID 58574313, compound

Product 1

HCID 58574552HCID 58574552, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 8-((3-fluorophenyl)ethynyl)-2,3,4,5-tetrahydro-[1,4]diazepino[7,1-b]quinazolin-11(1H)-one (0.1 g, 0.3 mmol), methyl formate (22 mg, 1.2 mmol), and 2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (2.1 mg, 0.015 mmol) in toluene (3 mL) was stirred at room temperature for 12 h. The reaction mixture was quenched with saturated potassium bisulfate (5 mL). The solution was extracted with ethyl acetate (3×20 mL) and 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): 362 (M+H+); 1H NMR (300 MHz, CDCl3) δ 8.27-8.23 (m, 1H), 8.20-8.18 (d, J=6.24 Hz, 1H), 7.79-7.78 (m, 1H), 7.62-7.59 (m, 1H), 7.38-7.32 (m, 2H), 7.29-7.26 (m, 1H), 7.14-7.07 (m, 1H), 4.57-4.49 (m, 2H), 3.94-3.84 (m, 2H), 3.75-3.65 (m, 2H), 3.28-3.19 (m, 2H). mGluR5 PAM EC50: +++. Fold shift at 10 μM: ++.

Workup

  1. customThe reaction mixture was quenched with saturated potassium bisulfate (5 mL)
  2. extractionThe solution was extracted with ethyl acetate (3×20 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-eefd18d118004ad2b4e17fd5620fa471
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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