Ethyl Acetate → 3-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

HRID 422665ノート

反応式

HRID 422665 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30]C(=C)[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C[N+]1([O-])CC[O:36]CC1.[O-]S([O-])=O.[Na+].[Na+].CCO[C:49]([CH3:51])=[O:50]>>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:51]([CH2:49][OH:50])([OH:36])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

参加物

5

反応物 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 536290387-(8-Chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl)-2-phenylquinoline

生成物 1

HCID 536290393-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

実験手順

7-[8-Chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl]-2-phenylquinoline (0.26 mmol, 110 mg) was dissolved in 8 mL solution (THF:H2O=3:1) and charged with NMO (0.52 mmol, 0.18 mL, 50% aq. solution) and K2OsO4.H2O (0.26 mmol, 9.6 mg). The resulting mixture was stirred at rt overnight. The reaction was quenched with Na2SO3 (1.30 mmol, 164 mg), diluted with EtOAc (40 mL), washed with brine (30 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure to give the desired product as a yellow solid; MS (ES+): m/z 457/396 (10/1) [MH+].

後処理

  1. washwashed with brine (30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-adc187fe98a447af95920ea63e12ad09
出典データセット
uspto-grants-2012_01
特許番号
US08101613B2

反応ノート

読み込み中…