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

HRID 422665Notes

Reaction equation

HRID 422665 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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+].

Workup

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

Sources & evidence

ORD record
ord-adc187fe98a447af95920ea63e12ad09
Source dataset
uspto-grants-2012_01
Patent number
US08101613B2

Reaction notes

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