Triethylamine → HCID 136379936, 화합물

HRID 17505

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HRID 17505 반응식
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH3:35])[C:20]([C:33]#[N:34])=[C:21]2[C:25]=1[O:24][C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32])=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:19]([CH3:35])[C:20]([C:33]#[N:34])=[C:21]3[C:25]=2[O:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[OH:32])=[N:22]3)[CH2:4]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 1363799317-Fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 136379936HCID 136379936, 화합물수율 24.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

(3S)-3-(Dimethylamino)pyrrolidine (100 μl, 0.79 mmol) and triethylamine (220 μl) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-212) (204 mg, 0.59 mmol). The system was purged with nitrogen, then sealed up, and heated at 120° C. for 30 minutes. After cooling, the solvent was evaporated away under reduced pressure, then the resulting residue was dissolved in chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (97:3, v/v) gave a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (64 mg, 24%) as a pale yellow solid.

후처리

  1. customThe system was purged with nitrogen
  2. customsealed up
  3. temperatureAfter cooling
  4. customthe solvent was evaporated away under reduced pressure
  5. dissolutionthe resulting residue was dissolved in chloroform
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. washElution with a mixed solvent of chloroform/methanol (97:3
  10. customv/v) gave a main product
  11. washThis was washed with a mixed solvent of isopropyl ether and ethanol
  12. filtrationthe solid was collected by filtration

출처 및 근거

ORD 기록
ord-a863434d04ef44febea007493fc06517
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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