Potassium Carbonate → HCID 86679485, compound

HRID 1776527Notes

Reaction equation

HRID 1776527 reaction equation
Br[CH2:2][CH2:3][N:4]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)[S:5]([CH3:8])(=[O:7])=[O:6].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:21]1([CH2:20][O:19][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=2[N:4]([CH2:3][CH2:2][N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)[S:5]([CH3:8])(=[O:7])=[O:6])[C:13]([O:15][CH3:16])=[O:14])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 86679484HCID 86679484, compound

Product 1

HCID 86679485HCID 86679485, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of methyl 4-(N-(2-bromoethyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate (630 mg, 1.551 mmol), 1-methylpiperazine (155 mg, 1.551 mmol) and K2CO3 (321 mg, 2.326 mmol) in dry CH3CN (14 ml) was heated at 130° C. under microwave irradiation for 3 hours. After cooling the inorganic salts were filtered, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32% NH4OH 95/5/0.5) to give methyl 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)-methylsulfonamido)benzoate as a light brown oil (520 mg, 1.222 mmol, 79% yield, MS/ESI+ 426.0 [MH]+).

Workup

  1. temperatureAfter cooling the inorganic salts
  2. filtrationwere filtered
  3. customthe solvent was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32% NH4OH 95/5/0.5)

Sources & evidence

ORD record
ord-ecb3f2f19a7e4ef3bbd234ad9fb114b5
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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