2,6-dinitro-2H-indazole → HCID 68445628, compound

HRID 388921Notes

Reaction equation

HRID 388921 reaction equation
[N+]([N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10]2)=[N:5]1)([O-])=O.[N:16]1([CH2:22][CH2:23][NH2:24])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C1COCC1.C(OCC)(=O)C>[N:16]1([CH2:22][CH2:23][NH:24][C:12]2[C:11]3[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=3)[NH:5][N:4]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 3308402,6-dinitro-2H-indazoleHCID 4082852-Morpholinoethylamine

Product 1

HCID 68445628HCID 68445628, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dinitro-2H-indazole (1 mmol) (prepared by nitration of 6-nitroindazole; Wrzeciono, et al., E. Pharmazie, 1980, 35, 593-596) in dry THF (4 mL) at 0° C., 2-morpholin-4-yl-ethylamine (2 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The contents were diluted with ethyl acetate (20 mL), washed with water (2×10 mL), and brine (10 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield 3-(2-morpholin-4-yl-ethylamino)-6-nitro-1H-indazole as a brown solid, which was reduced to 3-(2-morpholin-4-yl-ethylamino)-1H-indazol-6-ylamine by hydrogenation following general procedure F.

Workup

  1. washwashed with water (2×10 mL), and brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a2b48f2e15ce4e9f91000d0d01a6ce9a
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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