D-Camphorsulfonic Acid → HCID 69812522, compound

HRID 888448

Reaction equation

HRID 888448 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([CH2:14][CH3:15])[CH2:12][CH2:11][NH:10][C:9]2=[O:16])=[CH:4][CH:3]=1.Br[C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[N:23]=1.[CH3:27]C1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O>C(O)(C)C>[Br:24][C:22]1[N:23]=[C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[C:9](=[O:16])[NH:10][CH2:11][CH2:12][N:13]3[CH2:14][CH3:15])=[CH:6][CH:7]=2)[C:19](=[O:26])[N:20]([CH2:25][CH3:27])[CH:21]=1

Participants

5

Reactant 3

HCID 65617D-Camphorsulfonic AcidHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 576251673-(4-Aminophenyl)-4-ethylpiperazin-2-one

Product 1

HCID 69812522HCID 69812522, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 33 (450 mg, 2.05 mmol), isopropanol (5 mL), 13 (603 mg, 2.26 mmol) and DL-10-camphorsulfonic acid (813 mg, 3.50 mmol), and the reaction mixture was then stirred at reflux for 16 h. After this time, the reaction mixture was cooled to room temperature, filtered and the filter cake washed with isopropanol (10 mL). The resulting solid was dissolved in methylene chloride/methanol (3:1), absorbed onto silica gel and purified by flash chromatography to afford 34 in 79% yield (654 mg) as an orange solid: mp 152-153° C.; 1H NMR (500 MHz, CDCl3) 8.28 (bs, 1H 7.73 (d, 2H, J=8.5 Hz), 7.43 (d, 2H, J=8.5 Hz), 6.74 (s, 1H), 5.90 (d, 1H, J=3.5 Hz), 4.12 (s, 1H), 3.60 (m, 1H), 3.52 (s, 3H), 3.36 (m, 1H), 3.12 (m, 1H), 2.60 (m, 2H), 2.28 (m, 1H), 1.00 (t, 3H, J=7.0 Hz); MS (ESI+) m/z 406.0 (M+H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureat reflux for 16 h
  4. filtrationfiltered
  5. washthe filter cake washed with isopropanol (10 mL)
  6. dissolutionThe resulting solid was dissolved in methylene chloride/methanol (3:1)
  7. customabsorbed onto silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7578d5d25cc34485b5cdb7958ec3a929
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Linked notes

Loading…