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

HRID 244152ノート

反応式

HRID 244152 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-661060d9e2354ba49b622f336f54e6bd
出典データセット
uspto-grants-2014_02
特許番号
US08653268B2

反応ノート

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