HCID 86611712, compound → HCID 178511638, compound

HRID 2239821Notes

Reaction equation

HRID 2239821 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[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>[NH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([NH:27][C:2]2[CH:3]=[C:4]([NH:11][C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 86611712HCID 86611712, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511638HCID 178511638, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To crude 6-chloro-N-(2,6-difluorophenyl)imidazo[1,2-b]pyridazin-8-amine (0.186 mmol) from 1a was added trans-1,4-diaminocyclohexane (1000 mg, 8.77 mmol). The mixture was allowed to melt at 160° C. for 24 hrs. The melt was then cooled, water was added, followed by extraction with dichloromethane. The organic layer was then concentrated in vacuo and the resulting residue purified by reverse phase preparative HPLC to provide 50.6 mg (46%) of the titled compound as a TFA salt. LC/MS, m/e 359 (M+1). HPLC Rt, 1.7 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. Examples prepared in a similar manner are indicated in Table 2.

Workup

  1. temperatureThe melt was then cooled
  2. extractionfollowed by extraction with dichloromethane
  3. concentrationThe organic layer was then concentrated in vacuo
  4. customthe resulting residue purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-18ea103a4bc54c78b8a10e96f9e2f7ed
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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