Potassium Carbonate → HCID 70979183, compound

HRID 1618934Notes

Reaction equation

HRID 1618934 reaction equation
CS(O[CH2:6][C:7]#[C:8][C:9]1[CH:21]=[CH:20][C:12]2[N:13]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[N:14]=[N:15][C:11]=2[C:10]=1[Cl:22])(=O)=O.[CH3:23][N:24]1[C:28](=[O:29])[CH2:27][NH:26][C:25]1=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[Cl:22][C:10]1[C:11]2[N:15]=[N:14][N:13]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:12]=2[CH:20]=[CH:21][C:9]=1[C:8]#[C:7][CH2:6][N:26]1[CH2:27][C:28](=[O:29])[N:24]([CH3:23])[C:25]1=[O:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1388512,4-Imidazolidinedione, 3-methyl-HCID 86713617HCID 86713617, compound

Product 1

HCID 70979183HCID 70979183, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

3-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]prop-2-yn-1-yl methanesulfonate (30 mg, 0.088 mmol), 3-methylimidazolidine-2,4-dione (20.15 mg, 0.177 mmol), and potassium carbonate (36.6 mg, 0.265 mmol) were combined in acetonitrile (1 ml) and heated at 50° C. for 24 hours. The mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with saturated aqueous ammonium chloride and brine. The organic extract was dried with sodium sulfate, filtered, concentrated in vacuo. The residue was purified by silica gel gradient chromatography (0-5% acetone/dichloromethane) to provide the titled compound: 1H NMR (500 MHz, d6-DMSO) δ 7.97 (d, J=8.6 Hz, 1H), 7.73 (d, J=8.6 Hz, 1H), 4.64 (d, J=7.3 Hz, 2H), 4.53 (s, 2H), 4.13 (s, 2H), 2.88 (s, 3H), 1.42-1.34 (m, 1H), 0.56 (m, 2H), 0.47 (m, 2H) ppm. LRMS m/z (M+H) 358.0 [calculated for C17H17ClN5O2: 358.8].

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with saturated aqueous ammonium chloride and brine
  3. extractionThe organic extract
  4. dry with materialwas dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (0-5% acetone/dichloromethane)

Sources & evidence

ORD record
ord-cf20bedbeb4b46d0aa544723874c6e7b
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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