HCID 86611748, compound → HCID 178466726, compound

HRID 2239866Notes

Reaction equation

HRID 2239866 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)[C:5]2[N:6]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[N:7]=1.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>O>[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:2]2[CH:3]=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)[C:5]3[N:6]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=3)[N:7]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 86611748HCID 86611748, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178466726HCID 178466726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2 dram reaction vial was added crude 6-chloro-N-(4-ethoxyphenyl)-2,3-dimethylimidazo[1,2-b]pyridazin-8-amine (0.013 g, 0.04 mmol) from 1b and trans-1,4-diaminocyclohexane (1.0 g, 8.0 mmol). The mixture was allowed to melt at 160° C. for 4 days. The melt was then cooled, diluted with water and extracted with dichloromethane. The organic layer was concentrated and then diluted with MeOH and then purified by preparative HPLC. This gave 0.005 g of the titled compound as a TFA salt. 1H NMR (500 MHz, MeOD) δ ppm 7.24 (2H, d, J=8.25 Hz), 7.00 (2H, d, J=8.80 Hz), 6.17 (1H, s), 4.05 (2H, q, J=6.96 Hz), 3.62-3.83 (1H, m), 3.02-3.21 (1H, m), 2.47 (3H, s), 2.42 (3H, s), 2.18-2.29 (2H, m, J=11.55 Hz), 2.03-2.14 (2H, m, J=12.65 Hz), 1.45-1.62 (2H, m), 1.39 (3H, t, J=6.87 Hz), 1.26-1.36 (2H, m). LC/MS, m/e 395 (M+1). HPLC Rt, 2.49 min. YMC ODSC18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. customIn a 2 dram reaction
  2. temperatureThe melt was then cooled
  3. extractionextracted with dichloromethane
  4. concentrationThe organic layer was concentrated
  5. additiondiluted with MeOH
  6. custompurified by preparative HPLC
  7. customHPLC Rt, 2.49 min
  8. customB=100, gradient time 4 min
  9. customhold at 100% B 1 min, flow rate 4 mL/min.

Sources & evidence

ORD record
ord-b6e7c9cfdd7d41128fab31708d1eb673
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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