Acetonitrile → HCID 136149991, compound

HRID 2263406Notes

Reaction equation

HRID 2263406 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[S:6][C:7]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)=[C:12]([F:22])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[C:39](#[N:41])[CH3:40]>>[F:22][C:12]1[CH:11]=[C:10]([O:9][CH2:8][C:7]2[S:6][C:5]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:4][C:3]=2[CH2:2][N:41]2[CH2:24][CH2:25][CH:26]([C:29]([F:32])([F:31])[F:30])[CH2:40][CH2:39]2)[CH:15]=[CH:14][C:13]=1[C:16]1[NH:20][C:19](=[O:21])[O:18][N:17]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 136149952HCID 136149952, compound

Product 1

HCID 136149991HCID 136149991, compound

Procedure

To a mixture of 136 mg of 3-{4-[4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-fluoro-phenyl}-4H-[1,2,4]oxadiazol-5-one in 17 mL of acetonitrile was added 48.6 mg of 4-trifluoropiperidine hydrochloride and 70 mg of potassium carbonate. The resulting mixture was stirred overnight and then concentrated under reduced pressure. It was then taken into dichloromethane and washed with water. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (dichloromethane 98/methanol 2) to give 51.6 mg of 3-{2-fluoro-4-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (dichloromethane 98/methanol 2)

Sources & evidence

ORD record
ord-078a6a4f65384435a5275840b7a91fa9
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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