홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dimethyl Sulfoxide → 2-Cyclopropyl-5-fluoromethyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17582
노트
인쇄 미리보기

반응식

HRID 17582 반응식
[CH3:1][NH:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.CS(C)=O.[CH:12]1([C:15]2[O:16][C:17]3[C:18](=[C:20]([C:33]#[N:34])[C:21]([CH2:31][F:32])=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:23]=3F)[N:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C>[Cl-].[Na+].O.C(OCC)(=O)C>[CH:12]1([C:15]2[O:16][C:17]3[C:18](=[C:20]([C:33]#[N:34])[C:21]([CH2:31][F:32])=[C:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:23]=3[N:5]3[CH2:6][CH2:7][C@H:3]([NH:2][CH3:1])[CH2:4]3)[N:19]=2)[CH2:13][CH2:14]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidineHCID 685846532-Cyclopropyl-7-fluoro-5-fluoromethyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685855242-Cyclopropyl-5-fluoromethyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 24%

시약·촉매·용매

2
HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

Under nitrogen atmosphere at 130° C., (3S)-3-(methylamino)pyrrolidine (85 μl, 801 μmol) was added to a dimethyl sulfoxide (7 ml) solution of 2-cyclopropyl-7-fluoro-5-fluoromethyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-293) (207 mg, 667 μmol) and triethylamine (121 μl, 867 μmol), followed by stirring at the same temperature for 30 minutes. After cooling, saturated brine was added to the reaction liquid, and the mixture liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane:methanol=5:1, v/v) to obtain a crude product of the entitled compound. The crude product of the entitled compound was dissolved in ethyl acetate, washed with an aqueous saturated sodium hydrogencarbonate solution, then the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the entitled compound (62 mg, 24%) as an amorphous substance.

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture liquid was extracted with ethyl acetate
  3. washNext, the combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, dichloromethane
  8. custommethanol=5:1, v/v) to obtain a crude product of the entitled compound
  9. washwashed with an aqueous saturated sodium hydrogencarbonate solution
  10. extractionthe aqueous layer was extracted with ethyl acetate
  11. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9070a3060ba74c2395ec1d40860fbb3b
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트