Pyrrolidine → HCID 136149992, compound

HRID 2263409Notes

Reaction equation

HRID 2263409 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1)[O:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH:22]=O.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C([BH3-])#N.[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=3)=[N:9][C:8]=2[CH2:22][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:24]=[CH:25][C:26]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 136149961HCID 136149961, compound

Product 1

HCID 136149992HCID 136149992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 50 mg of 5-[3-fluoro-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde in 2 mL of methanol was added 0.03 mL of pyrrolidine. The resulting solution was stirred at room temperature for 1.5 h then 13.5 mg of sodium cyanoborohydride was added. After stirring at room temperature for 4 h, the reaction mixture was concentrated under reduced pressure. Ethyl acetate/water was added to the residue. The organic layer was separated and the aqueous layer extracted three times with ethyl acetate. 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 80/methanol 20) to give 9 mg of 3-{2-fluoro-4-[4-pyrrolidin-1-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one as a beige solid.

Workup

  1. stirringAfter stirring at room temperature for 4 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionEthyl acetate/water was added to the residue
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (dichloromethane 80/methanol 20)

Sources & evidence

ORD record
ord-109aab1a51464501b55ed9bc7c9197e1
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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