HCID 44540868, compound → HCID 44539635, compound

HRID 1616031Notes

Reaction equation

HRID 1616031 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>C(N)C.CS(C)=O.CO>[CH3:6][N:7]([CH3:2])[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]([NH:10][CH2:11][CH3:12])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 44540868HCID 44540868, compound

Product 1

HCID 44539635HCID 44539635, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6341EthylamineSolventHCID 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 ethylamine (70% weight in water, 1 ml). The mixture was heated at 160° C. for 3 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 (5 mg) as an orange 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-9ac218cb4b2b4ff79ff842abaa2b4768
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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