Potassium Carbonate → HCID 67365468, compound

HRID 245727Notes

Reaction equation

HRID 245727 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[N:17]3[CH:18]=[CH:19][N:20]=[C:21]([CH3:22])[C:16]3=[C:15]([Br:23])[N:14]=2)[CH2:9]1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:23][C:15]1[N:14]=[C:13]([C@@H:10]2[CH2:11][CH2:12][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:9]2)[N:17]2[CH:18]=[CH:19][N:20]=[C:21]([CH3:22])[C:16]=12

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67364100HCID 67364100, compound

Product 1

HCID 67365468HCID 67365468, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-2-(3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-1-yl)-2-oxoethyl acetate (0.105 mmol, 40 mg) in methanol (4 ml) was added potassium carbonate (0.126 mmol, 17.40 mg). After stirring the reaction mixture at room temperature for one hour, the solids were removed by filtration and the filtrate concentrated in vacuo to give (R)-1-(3-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-1-yl)-2-hydroxyethanone (35.6 mg). Reaction of the latter compound (35.6 mg) and 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (50 mg) according to the procedure described in example 4 step 4c and purification using prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid) gave ((R)—N-(4-(3-(1-(2-hydroxyacetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide (25.8 mg).

Workup

  1. customthe solids were removed by filtration
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-35df8d1bc7c349fe96403459eaba477e
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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