Dimethyl Sulfoxide → HCID 68584974, compound

HRID 17573Notes

Reaction equation

HRID 17573 reaction equation
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH3:30])[CH2:27][CH2:28][CH3:29])=[O:25])[O:23][C:19]=2[C:18](F)=[C:17]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]=1[CH3:38])#[N:14].C(N(CC)CC)C>[Cl-].[Na+].O>[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH3:30])[CH2:27][CH2:28][CH3:29])=[O:25])[O:23][C:19]=2[C:18]([N:9]2[CH2:10][CH2:11][C@H:7]([N:6]([CH3:12])[CH3:5])[CH2:8]2)=[C:17]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:16]=1[CH3:38])#[N:14]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685854164-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-propyl-1,3-benzoxazole-2-carboxamide

Product 1

HCID 68584974HCID 68584974, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (49 μl, 383 μmol) was added at 140 to 150° C. to a dimethyl sulfoxide (5 ml) solution of 4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-propyl-1,3-benzoxazole-2-carboxamide (I-284) (112 mg, 319 μmol) and triethylamine (58 μl, 415 μmol), followed by stirring at the same temperature for 140 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under the reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane:methanol==10:1, v/v) to obtain the entitled compound (62 mg, 44%) as an amorphous substance.

Workup

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. washNext, the combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under the reduced pressure
  8. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane

Sources & evidence

ORD record
ord-8a1d1f10a4ae428382966140d5210012
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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