4-Ethoxyaniline → HCID 178466728, compound

HRID 2239862Notes

Reaction equation

HRID 2239862 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]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.CCOC1C=CC(N)=CC=1.[NH2:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36][CH2:35]1>O>[NH2:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([NH:40][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]([C:11]#[N:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 866117406-Chloro-8-(4-ethoxyphenylamino)imidazo[1,2-b]pyridazine-3-carbonitrileHCID 178511674HCID 178511674, compound

Product 1

HCID 178466728HCID 178466728, compoundYield 586%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2 dram reaction vial was added 6-chloro-8-(4-ethoxyphenylamino)imidazo[1,2-b]pyridazine-3-carbonitrile (0.055 g, 0.017 mmol) from 1c and trans-1,4-diaminocyclohexane (1.0 g, 8.0 mmol). The mixture was allowed to melt at 160° C. for 1.5 hrs. 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 to give 0.039 g of the title compound as a TFA salt. 1H NMR (500 MHz, Solvent) δ ppm 7.91 (1H, s), 7.23 (2H, d, J=8.80 Hz), 6.96 (2H, d, J=8.80 Hz), 5.96 (1H, s), 4.04 (4H, q, J=6.78 Hz), 3.61-3.80 (1H, m), 2.99-3.19 (1H, m), 2.16-2.35 (2H, m, J=11.55 Hz), 2.01-2.16 (2H, m, J=12.65 Hz), 1.47-1.65 (2H, m), 1.39 (3H, t, J=7.15 Hz), 1.24-1.36 (2H, m). LC/MS, m/e 392 (M+1). HPLC Rt, 2.69 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

Sources & evidence

ORD record
ord-0efb62589f664688aef1a51b003983ab
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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