Potassium Carbonate → HCID 117666963, compound

HRID 1526253Notes

Reaction equation

HRID 1526253 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:17]=[N:18][N:19]([CH2:21][CH2:22][OH:23])[CH:20]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9].[NH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:32])=[C:29]([OH:31])[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+].O.O>CN1CCCC1=O>[NH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:32])=[C:29]([CH:30]=1)[O:31][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:17]=[N:18][N:19]([CH2:21][CH2:22][OH:23])[CH:20]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 226414135-Amino-2-fluorophenolHCID 23713072Sodium chloride dihydrateHCID 117667243HCID 117667243, compound

Product 1

HCID 117666963HCID 117666963, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-chloro-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (790 mg), 5-amino-2-fluorophenol (442 mg), potassium carbonate (641 mg), and N-methylpyrrolidone (8 mL) was reacted at 100° C. for 2 hours. To the reactant was added a mixed solution of saturated brine:water (1:1), followed by extraction with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-80:20) to obtain 5-(5-amino-2-fluorophenoxy)-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (523 mg) as a pale brown solid.

Workup

  1. customwas reacted at 100° C. for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-80:20)

Sources & evidence

ORD record
ord-3134322645914a5fbc3a9a8c44ceab07
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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