Dimethyl Sulfoxide → HCID 68585410, compound

HRID 17383Notes

Reaction equation

HRID 17383 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]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[O:25][C:26]3[C:27](=[C:29](C#N)[C:30]([CH3:40])=[C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:32]=3F)[N:28]=2)=[O:23])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].[CH2:43]([N:45](CC)CC)C>[Cl-].[Na+].O>[C:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2([C:43]#[N:45])[NH:28][C:27]3[CH:29]=[C:30]([CH3:40])[C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:32]([N:9]4[CH2:10][CH2:11][C@H:7]([N:6]([CH3:12])[CH3:5])[CH2:8]4)[C:26]=3[O:25]2)=[O:23])[CH2:18][CH2:17]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68586350HCID 68586350, compound

Product 1

HCID 68585410HCID 68585410, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Under nitrogen atmosphere, a dimethyl sulfoxide (2 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (99 μl, 782 μmol) was added at 150° C. to a dimethyl sulfoxide (11 ml) solution of 2-[(4-acetylpiperazin-1-yl)carbonyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-119) (265 mg, 652 μmol) and triethylamine (118 μl, 848 μmol), followed by stirring at the same temperature for 5 hours. 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, 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 (10:1, v/v) gave a crude product of the entitled compound as a solid, and the solid was suspended and washed in diisopropyl ether to obtain the entitled compound (72 mg, 22%) 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 reduced pressure

Sources & evidence

ORD record
ord-41326c096d774fa3b05e74d27b0fc659
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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