HCID 86611733, compound → HCID 178430602, compound

HRID 2239855Notes

Reaction equation

HRID 2239855 reaction equation
Cl[C:2]1[C:3]([CH3:19])=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]1>O.CO>[NH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([NH:27][C:2]2[C:3]([CH3:19])=[C:4]([NH:11][C:12]3[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=3)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 86611733HCID 86611733, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178430602HCID 178430602, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 2 dram reaction vial was added 3-(6-chloro-7-methylimidazo[1,2-b]pyridazin-8-ylamino)phenol (0.011 g, 0.028 mmol) from 1a and trans-1,4-diaminocyclohexane (1.0 g, 8.0 mmol). The mixture was allowed to melt at 160° C. for 24 hrs. The melt was then cooled, diluted with water and MeOH, and then purified by preparative HPLC to give 0.005 g of the title compound as a TFA salt. 1H NMR (400 MHz, MeOD) δ ppm 8.01 (1H, s), 7.73 (1H, s), 7.11 (1H, t, J=8.14 Hz), 6.48 (1H, d, J=7.63 Hz), 6.28 (1H, s), 3.88-4.10 (1H, m), 3.05-3.27 (1H, m), 2.24-2.37 (2H, m, J=8.65 Hz), 2.11-2.23 (5H, m), 1.45-1.70 (4H, m). LC/MS, m/e 353 (M+1). HPLC Rt, 1.20 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. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-71d1ab3534a7426a8c163d8d83ae8ce8
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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