2-(4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile → HCID 178511083, compound

HRID 1483848Notes

Reaction equation

HRID 1483848 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([NH:17][CH:18]4[CH2:23][CH2:22][C:21](=[CH:24][C:25]#[N:26])[CH2:20][CH2:19]4)[CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([NH:17][C@H:18]4[CH2:19][CH2:20][C@H:21]([CH2:24][C:25]#[N:26])[CH2:22][CH2:23]4)[CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 712277332-(4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile

Product 1

HCID 178511083HCID 178511083, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexylidene)acetonitrile (100 mg, 0.26 mmol) and 10% Pd/C (100 mg) in EtOAc (2 mL) was stirred under H2 balloon at room temperature for 4 h. LCMS showed the most of s.m was consumed. The mixture was filtered and the filterate was concentrated in vacuo. The residue was purified by prep. HPLC to give EX. 8-87 (13 mg, 13.7%) as a white solid.

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. concentrationthe filterate was concentrated in vacuo
  4. customThe residue was purified by prep
  5. customHPLC to give EX

Sources & evidence

ORD record
ord-c821e8012be94d2b986d1d14afb64687
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…