Potassium Carbonate → HCID 22036594, compound

HRID 1790093Notes

Reaction equation

HRID 1790093 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C>[N:23]1([CH2:22][CH2:21][N:8]2[C:9]3[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=3)[CH:6]=[N:7]2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 180574-NitroindazoleHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 22036594HCID 22036594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Nitroindazole (1.00 g, 6.13 mmol) and potassium carbonate (2.55 g, 18.4 mmol) in 15 mL of DMF was stirred for 30 min, after which 4-(2-chloro-ethyl)-morpholine hydrochloride (1.71 g, 9.19 mmol) was added. The reaction mixture was 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 combined 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 2.41 (m, 4 H), 2.79 (t, J=6.27 Hz, 2 H), 3.44 (m, 4 H), 4.66 (t, J=6.27 Hz, 2 H), 7.65 (m, 1 H), 8.17 (m, 1 H), 8.29 (m, 1 H), 8.52 (s, 1 H); MS (DCI/NH3) m/z 277 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ac0520d769764bfc91c80e44d5ffe0eb
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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