Dimethylformamide → (S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388095ノート

反応式

HRID 388095 の反応式
Br[C:2]1[N:3]=[C:4]2[N:10]([C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:9](=[O:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.BrC1N=C2N([C@H:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])C(=O)NC2=NC=1.C(=O)([O-])[O-].[Cs+].[Cs+].COS(OC)(=O)=O.[CH3:53][N:54](C)C=O>>[CH3:20][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:39]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:34]=3[CH:32]=[CH:33][CH:53]=[N:54]4)[N:3]=[C:4]2[N:10]([C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]1=[O:19]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-olHCID 86626387(S)-5-Bromo-1-methyl-3-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

生成物 1

HCID 66699676(S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one収率 83%

反応条件

温度
55 °C

実験手順

(S)-5-Bromo-1-methyl-3-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. To a solution of (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.300 g, 0.943 mmol) in dimethylformamide (3 mL) was added cesium carbonate (excess) followed by dimethylsulfate (0.130 g, 1.03 mmol). The solution was heated to 55° C. in a screw capped tube. After one hour, the solution was filtered to remove cesium carbonate salts. The filtrate was condensed under reduced pressure and the crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes) to afford the title compound (0.306 g, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.57 (d, 2H), 7.32 (m, 3H), 5.77 (q, 1H), 3.42 (s, 3H), 2.04 (d, 3H); 13C NMR (75 MHz, CHCl3) δ 52.6 (C═O); MS (ESI) m/z 333.3 [M+1]+, 335.3 [M+2]+.

後処理

  1. customcapped tube
  2. filtrationthe solution was filtered
  3. customto remove cesium carbonate salts
  4. customcondensed under reduced pressure
  5. customthe crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-1890afea18c54a2f835af4390df6a463
出典データセット
uspto-grants-2013_02
特許番号
US08372976B2

反応ノート

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