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

Dimethyl Sulfoxide → N-(6-methoxypyrazin-2-yl)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide

HRID 1666358
노트
인쇄 미리보기

반응식

HRID 1666358 반응식
Cl.N1C[CH2:6][C:5](=[C:8]2[CH:24]=[CH:23][CH:22]=[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=3)[CH:9]2C)CC1.[CH3:26][O:27][C:28]1[N:33]=[C:32]([NH:34]C(=O)OC2C=CC=CC=2)[CH:31]=[N:30][CH:29]=1.[CH:44]([N:47]([CH:50]([CH3:52])C)[CH2:48][CH3:49])(C)C.CS(C)=[O:55]>>[CH3:26][O:27][C:28]1[N:33]=[C:32]([NH:34][C:44]([N:47]2[CH2:48][CH2:49][C:6](=[CH:5][C:8]3[CH:24]=[CH:23][CH:22]=[C:10]([O:11][C:12]4[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][N:13]=4)[CH:9]=3)[CH2:52][CH2:50]2)=[O:55])[CH:31]=[N:30][CH:29]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 66875760Phenyl (6-methoxypyrazin-2-yl)carbamateHCID 668763562-(3-Piperidin-4-ylidene-methyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride

생성물 1

HCID 24963360N-(6-methoxypyrazin-2-yl)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide수율 69%

반응 조건

온도
60 °C

실험 절차

A solution of 2-(3-piperidin-4-ylidene-methyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.371 g, 1.00 mmol) (from Example 1, Step 5) and phenyl 6-methoxypyrazin-2-ylcarbamate (0.245 g, 1.00 mmol, from Step 1) in DMSO (2.5 mL) was treated with diisopropylethylamine (0.155 g, 1.2 mmol) and heated to 60° C. After 3 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The residue was crystallized in a 1:1 mix of hexanes and ethyl ether to afford the title compound (310 mg, 69%) as white crystals. MS (APCI 10 V) AP+ 486.20; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (t, J=5.46 Hz, 2H) 2.44 (t, J=5.46 Hz, 2H) 3.46 (t, J=5.46 Hz, 2H) 3.55 (t, J=5.46 Hz, 2H) 3.86 (s, 3H) 6.37 (s, 1H) 7.02-7.04 (m, 2H) 7.10 (d, J=7.62 Hz, 1H) 7.20 (d, J=8.60, Hz, 1H) 7.38 (t, J=8.77 Hz, 1H) 7.81 (s, 1H) 8.20 (dd, J=8.59 Hz, 2.14 Hz, 1H) 8.55 (s, 1H) 8.58 (s, 1H) 9.25 (s, 1H).

후처리

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was crystallized in a 1:1
  9. additionmix of hexanes and ethyl ether

출처 및 근거

ORD 기록
ord-352ce4750d254ea3a9067945ebb4aee7
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트