Cyclohexylamine → 6-(2-chlorophenyl)-7-(4-chlorophenyl)-N-cyclohexyl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine

HRID 2266307Notes

Reaction equation

HRID 2266307 reaction equation
Cl[C:2]1[N:6]2[N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][N:3]=1.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:8]1[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[CH:10][C:5]2[N:6]([C:2]([NH:31][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[N:3][N:4]=2)[N:7]=1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 579797573-Chloro-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 119832216-(2-chlorophenyl)-7-(4-chlorophenyl)-N-cyclohexyl-[1,2,4]triazolo[4,3-b]pyridazin-3-amineYield 41%

Conditions

Temperature
100 °C

Procedure

A suspension of 3-chloro-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine (38 mg, 0.1 mmol) in cyclohexylamine (0.5 mL) was stirred at 100° C. for 16 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (30 mL), washed with H2O, saturated aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (12 g) eluting with a gradient of EtOAc (40-100%) in hexanes to afford 18 mg (41%) of the title compound as a yellow powder. HPLC/MS (method A): retention time=3.58 min, (M+H)+=438.1. 1H NMR (CDCl3, 400 MHz): δ 7.87 (s, 1H), 7.35-7.43 (m, 3H), 7.30-7.33 (m, 1H), 7.20 (d, J=8.56 Hz, 2H), 7.04 (d, J=8.31 Hz, 2H), 4.83 (s, 1H), 3.98 (s, 1H), 2.22-2.25 (m, 2H), 1.79 (dd, J=9.78, 3.67 Hz, 2H), 1.63-1.72 (m, 1H), 1.41-1.52 (m, 2H), 1.27-1.39 (m, 2H), 1.21-1.26 (m, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (30 mL)
  4. washwashed with H2O, saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified
  9. washeluting with a gradient of EtOAc (40-100%) in hexanes

Sources & evidence

ORD record
ord-85f75df4284d4c98bcafd28391b59858
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

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