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

Cesium fluoride → HCID 25182570, 화합물

HRID 500737
노트
인쇄 미리보기

반응식

HRID 500737 반응식
C(OC([N:8]([C:16]1[C:21]([O:22][CH3:23])=[N:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][N:17]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.[F:33][CH:34]([F:53])[CH2:35][N:36]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][N:44]=[C:43]([NH:47][CH2:48][CH2:49][C:50]#[N:51])[N:42]=2)[C:38](I)=[N:37]1.[F-].[Cs+].[I-]>C(COC)OC>[NH2:8][C:16]1[N:17]=[CH:18][C:19]([C:38]2[C:39]([C:41]3[CH:46]=[CH:45][N:44]=[C:43]([NH:47][CH2:48][CH2:49][C:50]#[N:51])[N:42]=3)=[CH:40][N:36]([CH2:35][CH:34]([F:53])[F:33])[N:37]=2)=[N:20][C:21]=1[O:22][CH3:23]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 25953Cesium fluorideHCID 30165Iodide IonHCID 57856249HCID 57856249, 화합물HCID 57856300HCID 57856300, 화합물

생성물 1

HCID 25182570HCID 25182570, 화합물

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of the crude di-tert-butyl[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl]imidodicarbonate B-79-3 (0.6 mmol) in dimethoxyethane (2.5 mL) was added 3-{4-[1-(2,2-Difluoro-ethyl)-3-iodo-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-propionitrile B-33-3 (150 mg, 0.37 mmol) and Cesium Fluoride (1.1 mL of a 1M aqueous solution, 1.1 mmol). The resulting mixture was deoxygenated with a nitrogen bubbler for 5 min and then 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (15 mg, 0.019 mmol) was added. The mixture was then heated in an 80° C. oil bath for 20 hours. LCMS indicated the iodide had been completely consumed. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and reduced to minimum volume. The residue was taken up in dimethoxyethane (3 mL) and then heated at 170° C. in the microwave for 25 minutes to thermolyze the tert-butoxycarbonyl groups. The resulting dark mixture was filtered through a 0.45μ filter and the filtrate reduced to minimum volume. The residue was purified by HPLC to give 59 mg (37%) of B-79 as a fluffy white solid after lyophilization of the desired fractions. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 8.17 (s, 1H), 8.15 (d, J=5.05 Hz, 1H), 7.83 (s, 1H), 6.72 (d, J=5.31 Hz, 1H), 6.27 (tt, J=54.98, 3.76 Hz, 1H), 5.91 (br.t, J=5.18 Hz, 1H), 5.34 (br. s., 2H), 4.59 (td, J=14.65, 3.79 Hz, 2H), 3.76 (s, 3H), 3.55 (q, J=6.23 Hz, 2H), 2.64 (t, J=6.44 Hz, 2H)

후처리

  1. customThe resulting mixture was deoxygenated with a nitrogen bubbler for 5 min
  2. addition1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (15 mg, 0.019 mmol) was added
  3. customhad been completely consumed
  4. customThe mixture was partitioned between ethyl acetate and water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. temperatureheated at 170° C. in the microwave for 25 minutes
  8. filtrationThe resulting dark mixture was filtered through
  9. filtrationa 0.45μ filter
  10. customThe residue was purified by HPLC
  11. customto give 59 mg (37%) of B-79 as a fluffy white solid after lyophilization of the desired fractions

출처 및 근거

ORD 기록
ord-68cc65dea29141e3bc635f467cf163df
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772246B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트