Hydrochloric Acid → HCID 178423682, compound

HRID 1262355Notes

Reaction equation

HRID 1262355 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=3[N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])[N:6]2[N:5]=1)=O.[OH-:26].[Na+].Cl>>[OH:26][C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=3[N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])[N:6]2[N:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66712445N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide

Product 1

HCID 178423682HCID 178423682, compound

Conditions

Temperature
80 °C

Procedure

A mixture of N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide (315 mg, 0.832 mmol) in 5M NaOH (10 mL, 10 mmol) was stirred at 80° C. After 3 h, HPLC and MS showed product formation with no SM. The mixture was cooled to RT and pH of the solution was adjusted to 4 by adding HCl. The mixture was repeatedly extracted from EtOAc. Combined organic was washed with brine and was dried over magnesium sulfate. After solvent evaporation, N-[2-(2-Hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-methyl-phenyl]-N-methyl-methanesulfonamide was isolated as a solid (153 mg, 55%). LCMS (E/I+) 333 (M+H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionThe mixture was repeatedly extracted from EtOAc
  3. washCombined organic was washed with brine
  4. dry with materialwas dried over magnesium sulfate
  5. customAfter solvent evaporation

Sources & evidence

ORD record
ord-70e8f4c7f0a1486e98e6e5d20cceb1de
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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