Potassium Hydroxide → 4-(2-((5-nitro-1H-indazol-3-yl)oxy)ethyl)morpholine

HRID 1771399Notes

Reaction equation

HRID 1771399 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[N:12](C(OCC)=O)[N:11]=2)[CH2:3][CH2:2]1.[OH-].[K+]>CCO.O>[N+:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[O:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90004995HCID 90004995, compound

Product 1

HCID 900020924-(2-((5-nitro-1H-indazol-3-yl)oxy)ethyl)morpholineYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the morpholinoethoxy indazole described above (combined with a previous batch made in an identical manner) (309 mg, 0.848 mmol) in EtOH (2.0 mL) was added a solution of KOH (48 mg, 0.848 mmol) in water (1.0 mL) and the reaction mixture maintained at RT for 16 hr. The reaction mixture was then purified directly, without work-up, by SCX capture and release to afford 4-(2-((5-nitro-1H-indazol-3-yl)oxy)ethyl)morpholine as a bright yellow solid (221 mg, 86%); Rt 0.94 min (Method 2, acidic); m/z 293 (M+H)+ (ES+).

Workup

  1. customThe reaction mixture was then purified directly, without work-up, by SCX capture and release

Sources & evidence

ORD record
ord-852cd00dd74c41d890b61f4546126d45
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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