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Triethylamine → Ethyl (1R*,2R*)-2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}cyclopropanecarboxylate

HRID 17509
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인쇄 미리보기

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HRID 17509 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C@@H:12]3[CH2:14][C@H:13]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:11][C:7]=2[C:6](F)=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:4]=1[CH3:27])#[N:2].C(N(CC)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>CS(C)=O>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([C@@H:12]3[CH2:14][C@H:13]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:11][C:7]=2[C:6]([N:39]2[CH2:40][CH2:41][C@H:37]([N:36]([CH3:42])[CH3:35])[CH2:38]2)=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:4]=1[CH3:27])#[N:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 86630862Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate

생성물 1

HCID 86630861Ethyl (1R*,2R*)-2-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}cyclopropanecarboxylate수율 42%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
95 °C

실험 절차

Ethyl (1R*,2R*)-2-[4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-yl]cyclopropanecarboxylate (I-216) (200 mg, 0.55 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (146 μl, 1.10 mmol) and (3S)-3-(dimethylamino)pyrrolidine (146 μl, 1.15 mmol) were added, followed by stirring at 95° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative TLC. The eluate with chloroform/methanol (5:1, v/v) gave the entitled compound (105 mg, 42%) as a red brown solid.

후처리

  1. temperatureAfter cooled
  2. concentrationthis was concentrated under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-5fd2e993019f4c2ea0af983b8846a64f
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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