Dimethyl sulfoxide methanol → HCID 44539632, compound

HRID 1616029Notes

Reaction equation

HRID 1616029 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.CS(C)=O.[CH3:34][OH:35]>N1CCOCC1>[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[CH2:6][CH2:5][O:35][CH2:34][CH2:2]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 22036561Dimethyl sulfoxide methanolHCID 44540868HCID 44540868, compound

Product 1

HCID 44539632HCID 44539632, compound

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

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 morpholine (0.5 ml). The mixture was heated at 160° C. for 2 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 (16 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-986cdd2aa3454917b846df2a45b0f1b9
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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