Dimethyl Sulfoxide → 3-(4-Bromo-phenylsulfanyl)-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 1992435ノート

反応式

HRID 1992435 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:8](=[S:28])[NH:9][C:10]=2[C:11]2[C:20]([F:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.F[B-](F)(F)F.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([N+]#N)=[CH:37][CH:36]=1.CS(C)=O>C(Cl)Cl>[Br:34][C:35]1[CH:40]=[CH:39][C:38]([S:28][C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[C:20]([F:21])=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:18]4)=[CH:13][CH:12]=3)[N:9]=2)=[CH:37][CH:36]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 2734810Benzenediazonium, 4-bromo-, tetrafluoroborate(1-) (1:1)HCID 167536808-Amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazine-3-thiol

生成物 1

HCID 167536793-(4-Bromo-phenylsulfanyl)-1-(8-fluoro-2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-8-ylamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Into a round bottom flask was added 8-amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazine-3-thione (21 mg, 0.000053 mol), 4-bromobenzenediazonium tetrafluoroborate (0.018 g, 0.000064 mol) and dimethyl sulfoxide (0.1 mL, 0.002 mol) and the reaction mixture was stirred in ice for 30 min. The reaction mixture was cooled, dissolved in DCM and washed with water. Purification by Gilson HPLC eluting with 10→90% acetonitrile: H2O afforded the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.13-7.17 (m, 2H), 7.23 (d, J=5.05 Hz, 1H), 7.42 (d, J=8.59 Hz, 2H), 7.49-7.59 (m, 3H), 7.61 (d, J=5.05 Hz, 1H), 7.75-7.78 (m, 2H), 8.05 (d, J=8.59 Hz, 1H), 8.22-8.27 (m, 2H), 8.32 (dd, J=8.72, 1.39 Hz, 1H). MS (ES+): m/z 544.15 (100)[MH+]. HPLC: tR=2.69 min (Open Lynx polar—5 min).

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. customPurification by Gilson HPLC
  4. washeluting with 10→90% acetonitrile

出典と根拠

ORDレコード
ord-6f75fc8ef95841bb8ed91d0cb34d7214
出典データセット
uspto-grants-2010_01
特許番号
US07648987B2

反応ノート

読み込み中…