Dimethyl Sulfoxide → HCID 68587355, compound

HRID 17382Notes

Reaction equation

HRID 17382 reaction equation
F[C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]2[C:10]=1[O:9][C:8](C(N1CCOCC1)=O)=[N:7]2.C([N:30]([CH2:33]C)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1.[C:43]([O:46][CH2:47][CH3:48])(=O)[CH3:44].CS(C)=[O:51]>[Cl-].[Na+].O>[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][N:39]([C:2]2[C:3]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]3[C:10]=2[O:9][CH2:8][N:7]3[C:33]([N:30]2[CH2:48][CH2:47][O:46][CH2:43][CH2:44]2)=[O:51])[CH2:38]1

Participants

7

Reactant 5

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685848967-Fluoro-5-methyl-2-(morpholin-4-ylcarbonyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68587355HCID 68587355, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

7-Fluoro-5-methyl-2-(morpholin-4-ylcarbonyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-118) (40 mg, 0.11 mmol) was dissolved in dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (20 μl, 0.14 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (17 μl, 0.13 mmol) dissolved in dimethyl sulfoxide (0.5 ml) was added all at a time, followed by further stirring for 1 hour. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (33.7 mg, 67%) as a yellow gel.

Workup

  1. additionwas added all at a time
  2. temperatureThe mixture liquid was cooled to room temperature
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-d25d2ddc2def4a4dbc4cdbdc29dee386
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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