Potassium Carbonate → HCID 58438633, compound

HRID 1898611Notes

Reaction equation

HRID 1898611 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:40])[C@H:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]#[C:27][Si](C)(C)C)[N:24]=3)[N:19]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[CH:18]=2)=[O:16])[CH:11]2[CH2:13][CH2:12]2)[CH2:5][CH2:4]1)#[N:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:40])[C@H:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]#[CH:27])[N:24]=3)[N:19]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[CH:18]=2)=[O:16])[CH:11]2[CH2:12][CH2:13]2)[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67386575HCID 67386575, compound

Product 1

HCID 58438633HCID 58438633, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylsilanylethynyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide (400 mg, 0.69 mmol) in MeOH (8 mL) at room temp was added K2CO3 (10 mg, 0.072 mmol). The reaction mixture was stirred at room temp for 30 min then concentrated. The residue was dissolved in CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (50% to 100% EtOAc/hexanes) to afford 310 mg (89%) of 2-ethynyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide as a light brown foamy solid. NMR showed a trace of 5-Cl pyrrolopyrazine present.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-21b91616081e465291d8ed23e015f2b7
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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