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

Triethylamine → Methyl 1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]-4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate

HRID 255292
노트
인쇄 미리보기

반응식

HRID 255292 반응식
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH:24]3[C:29]([O:31][CH3:32])=[O:30])[C:14]=2[CH:33]=1)#[N:9].[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1/[CH:42]=[CH:43]/[CH:44]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO.C(OCC)(=O)C.O>[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1/[CH:42]=[CH:43]/[CH2:44][N:26]1[CH2:27][CH2:28][CH:23]([CH2:22][CH2:21][CH2:20][N:15]2[C:14]3[CH:33]=[C:10]([C:8]#[N:9])[CH:11]=[CH:12][C:13]=3[O:18][CH2:17][C:16]2=[O:19])[CH:24]([C:29]([O:31][CH3:32])=[O:30])[CH2:25]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66774489methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate trifluoroacetate2회HCID 86642138(2E)-3-(2,5-difluorophenyl)-2-propenal

생성물 1

HCID 15982403Methyl 1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]-4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate
수율 32.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21584188Chloroform methanol용매

반응 조건

온도
0 °C

실험 절차

A solution of methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate trifluoroacetate (Intermediate 130, crude, 171, 0.48 mmol), (2E)-3-(2,5-difluorophenyl)acrylaldehyde [FR 2872164] (81 mg, 0.48 mmol), and triethylamine (0.13 mL. 0.96 mmol) in chloroform/methanol (6 mL, 10:1) was heated over 3 Å molecular sieves at 70° C. for 3 hours. The reaction mixture was cooled to 0° C., and sodium triacetoxy borohydride (200 mg, 0.94 mmol) was added. The resulting reaction mixture was allowed to warm to room temperature and stir for 18 hours. The reaction was diluted with ethyl acetate (25 mL) and water (10 mL). The aqueous phase was separated and washed twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate and evaporated at reduced pressure. Chromatography on silica gel with diethyl ether gave the title compound as a off-white foam, (79 mg, 32%).

후처리

  1. customThe resulting reaction mixture
  2. temperatureto warm to room temperature
  3. customThe aqueous phase was separated
  4. washwashed twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at reduced pressure

출처 및 근거

ORD 기록
ord-2feeb24140a443faa3b7acbb16cd6a45
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07875715B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트