2,6-Lutidine → HCID 57799150, compound

HRID 2100346Notes

Reaction equation

HRID 2100346 reaction equation
C(Cl)(=O)C(Cl)=O.C[Si](COCC[N:15]1[C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=[N:16]1)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[C:31]1[C:32]([NH2:38])=[N:33][C:34]([NH2:37])=[CH:35][N:36]=1.N1C(C)=CC=CC=1C>ClCCl.CN(C)C=O.C(#N)C>[NH2:38][C:32]1[N:33]=[C:34]([NH:37][C:20]([C:19]2[NH:15][N:16]=[CH:17][CH:18]=2)=[O:22])[CH:35]=[N:36][C:31]=1[C:25]1[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]=1[Cl:23]

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 65578Oxalyl chlorideHCID 18180195HCID 18180195, compoundHCID 673989261-[2-[(Trimethylsilyl)methoxy]ethyl]-1H-pyrazole-5-carboxylic acid

Product 1

HCID 57799150HCID 57799150, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.17 ml, 1.9 mmol) was added to a slurry of 2-(2-trimethylsilanylmethoxy-ethyl)-2H-pyrazole-3-carboxylic acid) (Heterocycles (1992) 34 303-314), (428 mg, 1.76 mmol) in dichloromethane (15 ml), 1 drop of dimethylformamide was added and the reaction stirred at room temperature under N2 for 1 hour before concentrating in vacuo and azeotroping with dichloromethane. The resulting acid chloride was dissolved in 5 ml acetonitrile and added to a solution of 3-(2,5-dichloro-phenyl)pyrazine-2,6-diamine (Preparation 11, 300 mg, 1.18 mmol) in acetonitrile (15 ml) and 2,6-lutidine (0.21 ml, 1.8 mmol). The reaction was stirred at room temperature under N2 for 72 hours before concentrating in vacuo then partitioning between 50 ml ethyl acetate and 50 ml water. The organic layer was dried over MgSO4 and concentrated in vacuo to give a brown oil which was purified by column chromatography (ethyl acetate, heptane, 1:2) to give 52 mg of the title product.

Workup

  1. concentrationbefore concentrating in vacuo
  2. customazeotroping with dichloromethane
  3. dissolutionThe resulting acid chloride was dissolved in 5 ml acetonitrile
  4. stirringThe reaction was stirred at room temperature under N2 for 72 hours
  5. concentrationbefore concentrating in vacuo
  6. customthen partitioning between 50 ml ethyl acetate and 50 ml water
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give a brown oil which
  10. customwas purified by column chromatography (ethyl acetate, heptane, 1:2)

Sources & evidence

ORD record
ord-33a657c2ac13400dadb592821632972f
Source dataset
uspto-grants-2009_08
Patent number
US07572797B2

Reaction notes

Loading…