Dimethylformamide → 4-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione

HRID 63844

반응식

HRID 63844 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:34]([F:37])([F:36])[F:35])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:30][C:29](=[O:31])[NH:28][C:27](=[O:32])[CH2:26]4)=[O:24])=[C:19]([CH3:33])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:38][C:39]([F:44])([F:43])[CH2:40][CH2:41]I.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O.CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:34]([F:35])([F:36])[F:37])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:30][C:29](=[O:31])[N:28]([CH2:41][CH2:40][C:39]([F:44])([F:43])[F:38])[C:27](=[O:32])[CH2:26]4)=[O:24])=[C:19]([CH3:33])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 1180473454-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]piperazine-2,6-dione

생성물 1

HCID 1180469544-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Into a 50-mL round-bottom flask, was placed 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]piperazine-2,6-dione (200 mg, 0.36 mmol, 1.00 equiv), 1,1,1-trifluoro-3-iodopropane (163.5 mg, 0.73 mmol, 2.00 equiv), N,N-dimethylformamide (10 mL), potassium carbonate (100.7 mg, 0.73 mmol, 2.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 60 mL of H2O. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 4×40 mL of brine. The mixture was dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The crude product (85 mg) was purified by Prep-HPLC. This resulted in 39.5 g (17%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione as a white solid. (ES, m/z): [M+CH3CN]+ 685.0; 1H NMR (300 MHz, CDCl3): δ 7.85 (s, 1H), 7.78 (s, 1H), 7.72 (s, 1H), 7.61 (d, J=8.7 Hz, 2H), 7.28-7.23 (m, 1H), 4.79 (s, 2H), 4.19-4.10 (m, 5H), 3.75 (d, J=17.4 Hz, 1H), 2.49-2.41 (m, 2H), 2.32 (s, 3H)

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
  3. washThe resulting mixture was washed with 4×40 mL of brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThe crude product (85 mg) was purified by Prep-HPLC
  7. customThis resulted in 39.5 g (17%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione as a white solid

출처 및 근거

ORD 기록
ord-3c0edb98e0984d3f84d2f6393ee72000
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447084B2

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