HCID 44540868, compound → HCID 44539733, compound

HRID 1616030Notes

Reaction equation

HRID 1616030 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[C:5](F)=[CH:4][CH:3]=1>N1CCCCC1.CS(C)=O.CO>[CH3:8][N:10]([CH3:11])[C:5]1[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])=[N:7][C:2]([N:7]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 44540868HCID 44540868, compound

Product 1

HCID 44539733HCID 44539733, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
160 °C

Procedure

6-Chloro-3-fluoro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (50 mg, 0.12 mmol) was placed in a microwave vial and dissolved in piperidine (0.5 ml). The mixture was heated at 160° C. for 1 h under microwave irradiation. The solvent was removed under a stream of nitrogen to give a crude residue that was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with MeOH and the solvent removed under a stream of nitrogen to give the title compound (7 mg) as a yellow solid.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. customto give a crude residue that
  3. custompurified by Mass Directed Automated Preparative HPLC (Method C)
  4. washeluted with MeOH
  5. customthe solvent removed under a stream of nitrogen

Sources & evidence

ORD record
ord-dc5bccfb50014b7aa646006ee76e66a7
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…