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Triethylamine → 2-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-2-methylpropanamide

HRID 17353
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HRID 17353 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH3:17])([CH3:16])[C:13]([NH2:15])=[O:14])[O:11][C:7]=2[C:6](F)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2].C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1.C(OCC)(=O)C>CS(C)=O.O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH3:17])([CH3:16])[C:13]([NH2:15])=[O:14])[O:11][C:7]=2[C:6]([N:37]2[CH2:38][CH2:39][C@H:35]([N:34]([CH3:40])[CH3:33])[CH2:36]2)=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:25])#[N:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68585344HCID 68585344, 화합물

생성물 1

HCID 685849532-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-2-methylpropanamide수율 55%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

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온도
90 °C

실험 절차

2-(4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-2-methylpropanamide (I-96) (58 mg, 0.17 mmol) was dissolved in dimethyl sulfoxide (1.2 ml), triethylamine (33 μl, 0.24 mmol) and (3S)-3-(dimethylamino)pyrrolidine (26 μl, 0.21 mmol) were added, followed by stirring at 90° C. for 3 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) to obtain the entitled compound (41 mg, 0.09 mmol, 55%) as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. washeluted with a mixed solvent of chloroform/methanol (10:1

출처 및 근거

ORD 기록
ord-f4a9139ffa0e4494935e0ae65f9bb8ec
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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