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Methanol → HCID 90304553, compound

HRID 62457
Notes
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Reaction equation

HRID 62457 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([C:10]1[N:14]2[CH:15]=[CH:16][N:17]=[C:18]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[C:13]2=[C:12]([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[N:11]=1)[C:6]([O:8]C)=O)#[N:2].CO>CCO.[Ni]>[CH3:30][O:29][C:22]1[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=1[CH2:20][NH:19][C:18]1[C:13]2[N:14]([C:10]([CH:5]3[CH2:4][CH2:3][CH2:1][NH:2][C:6]3=[O:8])=[N:11][C:12]=2[C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=2)[CH:15]=[CH:16][N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 887MethanolHCID 90304033Methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate

Product 1

HCID 90304553HCID 90304553, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 4-(3-(4-cyano-1-methoxy-1-oxobutan-2-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (12 g, 22.1 mmol) in EtOH (350 mL) was added Ra—Ni (24 g) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (50 psi) at 75° C. for 7 hours. The reaction was complete detected by LCMS. The suspension was filtered through a pad of Celite and the pad was washed with EtOH (20 mL×3). The combined filtrates were concentrated. The residue was purified by column chromatography on silica gel eluted with DCM:MeOH=30:1 to give methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-oxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate (4.6 g, yield 40%).

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. filtrationThe suspension was filtered through a pad of Celite
  4. washthe pad was washed with EtOH (20 mL×3)
  5. concentrationThe combined filtrates were concentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with DCM

Sources & evidence

ORD record
ord-9451584972f74532876f40a018e6ef07
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446130B2

Reaction notes

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