Potassium Carbonate → HCID 22036586, compound

HRID 1790155Notes

Reaction equation

HRID 1790155 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25]>CN(C=O)C>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][CH2:21][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 943083-(Dimethylamino)propyl chloride hydrochloride

Product 1

HCID 22036586HCID 22036586, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-nitro-1H-indazole (0.500 g, 3.07 mmol) and potassium carbonate (0.889 g, 6.44 mmol) in 15.3 mL of DMF was stirred for 30 minutes after which (3-chloro-propyl)-dimethyl-amine hydrochloride (0.553 g 3.50 mmol) was added. The reaction mixture was then heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.97 (m, 2 H), 2.10 (m, 6 H), 2.14 (m, 2 H), 4.58 (t, J=6.78 Hz, 2 H), 7.99 (m, 2 H), 8.32 (m, 1 H), 8.74 (m, 1 H); MS (DCI/NH3) m/z 249 [M+H]+.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a plug of silica gel which
  4. washwas rinsed with triethylamine/ethyl acetate (1/4)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-423b9194011247918f05f636f46ac013
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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