Dimethyl Sulfoxide → HCID 52919896, compound

HRID 1423243Notes

Reaction equation

HRID 1423243 reaction equation
[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>CCOC(C)=O>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 66824947HCID 66824947, compound

Product 1

HCID 52919896HCID 52919896, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Into a 25 mL screw-cap vial were added 3-benzyl-1-(3-cyclobutyloxy-4-methoxy-phenyl)-piperazine (149 mg, 0.42 mmol), 2-chloropyrimidine (60 mg, 0.53 mmol), diisopropylethylamine (150 μL, 0.86 mmol), and DMSO (2 mL). The reaction mixture was heated at 100° C. for 12 h then cooled to room temperature. The reaction mixture was diluted with EtOAc and washed 3× with water followed by brine, concentrated, and adsorbed onto silica gel and purified by silica gel flash chromatography with a 0-50% EtOAc/Hexanes gradient to afford the title compound as a an off-white solid (43 mg, 23%). LC/MS (Method B) 4.62 min, [[M+1]+ 431

Workup

  1. customInto a 25 mL screw-cap vial
  2. temperaturethen cooled to room temperature
  3. washwashed 3× with water
  4. concentrationconcentrated
  5. custompurified by silica gel flash chromatography with a 0-50% EtOAc/Hexanes gradient

Sources & evidence

ORD record
ord-8a5a010f395a482596663951813f360d
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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