Cesium carbonate → HCID 86711924、化合物

HRID 1475231

反応式

HRID 1475231 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][C:8]1[N:12]([CH2:13][C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:11]=[C:10]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[N:22]=2)[N:9]=1.Br[CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CN(C=O)C.O>[CH3:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[CH:15]=2)[N:11]=[C:10]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=3)[N:22]=2)[N:9]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 133496544-BromotetrahydropyranHCID 86711921HCID 86711921、化合物

生成物 1

HCID 86711924HCID 86711924、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

A mixture of Cs2CO3 (62.5 mg, 0.192 mmol), 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenol (Example 59; 40.0 mg, 0.096 mmol) and 4-bromotetrahydro-2H-pyran (21.7 uL, 0.192 mmol) in DMF (0.48 mL) was heated at 140° C. for 1 h under microwave irradiation. The mixture was diluted with H2O and extracted with 4:1 CHCl3:i-PrOH. The organic layer was dried over MgSO4 and concentrated under reduced pressure; the residue was dissolved in DMSO and purified using Prep-HPLC to furnish the title compound; MS (ES+) C24H22F3N5O4 requires: 501. found 502 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.29 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 7.28 (m, 1H), 6.89 (dd, J=8.1, 2.4 Hz, 1H), 6.80 (m, 2H), 5.41 (s, 2H), 4.47 (m, 1H), 3.95 (m, 2H), 3.57 (m, 2H), 2.54 (s, 3H), 2.01 (m, 2H), 1.75 (m, 2H).

後処理

  1. extractionextracted with 4:1 CHCl3
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in DMSO
  5. custompurified

出典と根拠

ORDレコード
ord-f86210d8bbdf4a1995f69e72ea31a855
出典データセット
uspto-grants-2015_04
特許番号
US09018380B2

関連ノート

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