Urea → HCID 178429231、化合物

HRID 227723ノート

反応式

HRID 227723 の反応式
[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

参加物

6

反応物 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 178468064HCID 178468064、化合物

生成物 1

HCID 178429231HCID 178429231、化合物収率 8.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5141fa65610f4ff09271cae664d215cb
出典データセット
uspto-grants-2009_07
特許番号
US07560467B2

反応ノート

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