Dimethylformamide → 1-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]-3-(2,2,2-trifluoroethyl)imidazolidin-4-one

HRID 63856

反応式

HRID 63856 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:35]([F:38])([F:37])[F:36])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][C:28](=[O:30])[NH:27][CH2:26]4)=[O:24])=[C:19]([C:31]([F:34])([F:33])[F:32])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C)C=O.[H-].[Na+].FC(F)(F)S(O[CH2:52][C:53]([F:56])([F:55])[F:54])(=O)=O>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:35]([F:36])([F:37])[F:38])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][C:28](=[O:30])[N:27]([CH2:52][C:53]([F:56])([F:55])[F:54])[CH2:26]4)=[O:24])=[C:19]([C:31]([F:33])([F:34])[F:32])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 1180469091-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]imidazolidin-4-one

生成物 1

HCID 1180473681-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]-3-(2,2,2-trifluoroethyl)imidazolidin-4-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Into a 50-mL round bottom flask, was placed 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]imidazolidin-4-one (50 mg, 0.09 mmol, 1.00 equiv), N,N-dimethylformamide (1 mL), sodium hydride (7 mg, 0.17 mmol, 2.00 equiv, 60%), The resulting solution was stirred for 20 min at 25° C. Added 2,2,2-trifluoroethyl trifluoromethanesulfonate (40 mg, 0.17 mmol, 1.98 equiv). The resulting solution was allowed to react, with stirring, for an additional 1 h at r t. The reaction was then quenched by the addition of 10 ml of water. The resulting solution was extracted with 2×10 ml of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×10 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with PE/EA (2/1). This resulted in 23.7 mg (37%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]-3-(2,2,2-trifluoroethyl)imidazolidin-4-one as yellow oil. ES, m/z): [M+CH3CN]+697.0; 1H NMR (300 MHz, CDCl3): δ8.12-8.22 (m, 2H), 7.98 (s, 1H), 7.86 (d, J=7.8 Hz, 2H), 7.73 (d, J=7.8 Hz, 1H), 5.17 (s, 1H), 4.79 (s, 1H), 4.44 (d, J=18.0 Hz, 1H), 4.01-4.31 (m, 4H), 3.93 (s, 1H).

後処理

  1. customInto a 50-mL round bottom flask, was placed
  2. customto react
  3. customThe reaction was then quenched by the addition of 10 ml of water
  4. extractionThe resulting solution was extracted with 2×10 ml of ethyl acetate
  5. washThe resulting mixture was washed with 3×10 mL of brine
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThis resulted in 23.7 mg (37%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(trifluoromethyl)phenyl)carbonyl]-3-(2,2,2-trifluoroethyl)imidazolidin-4-one as yellow oil

出典と根拠

ORDレコード
ord-6a96ab6c665440a484c764721a7671f9
出典データセット
uspto-grants-2016_09
特許番号
US09447084B2

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