Urea → HCID 178429231, 화합물

HRID 227723노트

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HRID 227723 반응식
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15])[CH:9]=2)[NH:4][N:3]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.[NH2:27][C:28]([NH2:30])=[O:29].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>CC#N>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:13]3[CH:23]([C:22]4[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=4)[NH:27][C:28](=[O:29])[NH:30][C:14]=3[CH3:15])=[O:17])[CH:9]=2)[NH:4][N:3]=1

참가 물질

6

반응물 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 178468064HCID 178468064, 화합물

생성물 1

HCID 178429231HCID 178429231, 화합물수율 8.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

The product of Step (c) (330 mg, 1.11 mmol, 1 equiv), 4-fluorobenzaldehyde (120 uL, 1.13 mmol, 1.00 equiv), urea (100 mg, 1.67 mmol, 1.67 equiv), and Ytterbium triflate (70 mg, 0.12 mmol, 0.10 equiv) were combined in CH3CN (6 mL). The reaction vessel was sealed and heated to 100° C. for 18 hours. The reaction was cooled to room temperature and the precipitate was collected by filtration. The solid was washed with Et2O/CH3CN several times, then purified by preparative LC-MS to afford 40 mg (8%) of a white solid. 1H NMR (400 MHz, d6-DMSO) 13.3 (s, 1H), 9.69 (s, 1H), 8.77 (s, 1H), 7.96 (s, 1H), 7.62 (m, 1H), 7.48 (s, 2H), 7.35 (m, 2H), 7.17 (m, 2H), 5.43 (m, 1H), 2.07 (s, 3H).

후처리

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washThe solid was washed with Et2O/CH3CN several times
  5. custompurified by preparative LC-MS

출처 및 근거

ORD 기록
ord-5141fa65610f4ff09271cae664d215cb
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560467B2

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