Water → HCID 136150036, compound

HRID 2263431Notes

Reaction equation

HRID 2263431 reaction equation
[NH2:1][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.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].O>ClCCl>[F:22][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]1[NH:20][C:19](=[O:21])[O:18][N:17]=1)[O:9][CH2:8][C:7]1[S:6][C:5]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:25][CH:24]=2)=[N:4][C:3]=1[CH2:2][NH:1][C:39](=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 7918Acetic Anhydride2×HCID 136149941HCID 136149941, compound

Product 1

HCID 136150036HCID 136150036, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 53.3 mg of 3-{4-[4-aminomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-fluoro-phenyl}-4H-1,2,4-oxadiazol-5-one in 1 mL of dichloromethane was added 27 mg of pyridine and 19 mg of acetic anhydride. The resulting mixture was stirred for 1.5 h at room temperature and then a drop of pyridine and acetic anhydride were added. After stirring for 25 minutes at room temperature, it was poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from dichloromethane 100 to dichloromethane 90/methanol 10/water 1/acetic acid 1) to give 6.2 mg of N-[5-[3-fluoro-4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl]-acetamide.

Workup

  1. stirringAfter stirring for 25 minutes at room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (gradient from dichloromethane 100 to dichloromethane 90/methanol 10/water 1/acetic acid 1)

Sources & evidence

ORD record
ord-9c062eb16f2f41e39269fc4a9ae250bb
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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