Cesium carbonate → HCID 59028388, compound

HRID 2426804Notes

Reaction equation

HRID 2426804 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:13][NH:14][CH2:15][C:16]1(C)[CH2:18][CH2:17]1.[C:20](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([N:14]([CH3:13])[CH2:15][CH:16]2[CH2:18][CH:17]2[CH3:20])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 948302,6-Dichloroisonicotinic acidHCID 672498312712421-24-2

Product 1

HCID 59028388HCID 59028388, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dichloroisonicotinic acid (0.25 g, 1.3 mmol), methyl-[(methylcyclopropyl)methyl]amine hydrochloride (0.53 g, 3.9 mmol) and cesium carbonate (1.25 g, 6.5 mmol) in 5 mL DMF was heated to 120° C. in a sealed tube for 72 hr. The reaction was partitioned between 1M HCl and ethyl acetate. The organics were washed with water (4×), brine, dried over sodium sulfate, filtered and evaporated in vacuo to give 0.3 g (90%) of crude 2-chloro-6-{methyl[(2-methylcyclopropyl)methyl]amino}isonicotinic acid as a brown oil: LCMS (M+H)=255.0.

Workup

  1. customThe reaction was partitioned between 1M HCl and ethyl acetate
  2. washThe organics were washed with water (4×), brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-99912e004a9944b5a3eb907466340a34
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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