Dimethyl Sulfoxide → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-2-carbonitrile

HRID 17380Notes

Reaction equation

HRID 17380 reaction equation
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.F[C:14]1[C:15]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:16]([CH3:33])[C:17](C#N)=[C:18]2[C:22]=1[O:21][C:20]([C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])=[N:19]2.[CH2:40]([N:42](CC)CC)C>[Cl-].[Na+].O>[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][N:9]([C:14]2[C:22]3[O:21][C:20]([C:23]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])([C:40]#[N:42])[NH:19][C:18]=3[CH:17]=[C:16]([CH3:33])[C:15]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8]1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685850607-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685853927-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, a dimethyl sulfoxide (700 μl) solution of (3S)-3-(dimethylamino)pyrrolidine (24 μl, 192 μmol) was added at 150° C. to a dimethyl sulfoxide (2.5 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile (I-117) (58 mg, 160 μmol) and triethylamine (29 μl, 208 μmol), followed by stirring at the same temperature for 75 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (20:1, v/v) gave a crude product of the entitled compound as a solid, and the solid was recrystallized from diisopropyl ether/n-hexane to obtain the entitled compound (23 mg, 31%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cec825b544b24afb86a412823f6cf250
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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