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

Benzene → (S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate

HRID 2279551
노트
인쇄 미리보기

반응식

HRID 2279551 반응식
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C@H:9]1[C@H:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[F:29])C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:53]1[CH2:58][CH2:57][CH:56]([NH:59][C:60]2[N:61]=[CH:62][C:63]3[CH2:69][CH2:68][NH:67][CH2:66][C:64]=3[N:65]=2)[CH2:55][CH2:54]1.C[N:71]([CH:73]=[O:74])C>O>[F:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[C@H:15]([NH:71][C:73]([N:67]1[CH2:68][CH2:69][C:63]2[CH:62]=[N:61][C:60]([NH:59][CH:56]3[CH2:55][CH2:54][O:53][CH2:58][CH2:57]3)=[N:65][C:64]=2[CH2:66]1)=[O:74])[C@H:9]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 241BenzeneHCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 71743546N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amineHCID 86705537(S)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)acetic acid

생성물 1

HCID 86705539
(S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate
수율 74.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 322 (0.341 g, 0.813 mmol) and benzene (8 mL) cooled 0° C. was added TEA (0.154 mL, 1.11 mmol) and diphenylphosphoryl azide (0.239 mL, 1.11 mmol) and the reaction stirred at RT for 1 h then refluxed for 3 h. The reaction was then cooled to RT and a solution of 28 (0.200 g, 0.739 mmol), TEA (0.154 mL, 1.11 mmol) and DMF (3 mL) was added, and stirred at RT for 18 h. The reaction was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:10) to afford 0.360 g (74.9%) of (S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate (324).

후처리

  1. temperaturethen refluxed for 3 h
  2. temperatureThe reaction was then cooled to RT
  3. stirringstirred at RT for 18 h
  4. extractionextracted with DCM
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with DCM/MeOH (500:10)

출처 및 근거

ORD 기록
ord-e4abadf307384326803847c0cf18abf9
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133187B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트