Sodium Nitrate → HCID 67371453, compound

HRID 401994Notes

Reaction equation

HRID 401994 reaction equation
[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[N+:32]([O-])([O-:34])=[O:33].[Na+]>C(O)(C(F)(F)F)=O.O.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:9][C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:15]([N+:32]([O-:34])=[O:33])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 24268Sodium NitrateHCID 53373968HCID 53373968, compound

Product 1

HCID 67371453HCID 67371453, compoundYield 65.9%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 516892Sodium BicarbonateSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine (Example 14, 10 mmol, 4.24 g) in TFA (10 mL) was added sodium nitrate (12 mmol, 1.02 g) at 0° C. The mixture was allowed to warm up to room temperature and stirred for 8 hours. The mixture was then diluted with water/EtOAc, neutralized slowly with NaHCO3 powder. The organic layers were combined, dried, and condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% MeOH) to give a pale-yellow solid, 3-butyl-4-(4-cyclohexyloxy-3-nitro-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine (3.09 g).

Workup

  1. customdried
  2. customcondensed in vacuo
  3. customthe residue was purified by silica gel chromatography (DCM to DCM+10% MeOH)

Sources & evidence

ORD record
ord-7ba6dbff07fa46e1a780a23183ebc212
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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