Methylamine → HCID 57583999, compound

HRID 2361634Notes

Reaction equation

HRID 2361634 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C1N=C[N:13](C(N2C=NC=C2)=O)[CH:12]=1.CN.C1COCC1>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:13][CH3:12])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 27628725-Chloro-2-picolinic acid

Product 1

HCID 57583999HCID 57583999, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloropyridine-2-carboxylic acid (315 mg, 2.0 mmol) in DCE (2.5 ml) at 20 to 25° C. was added CDI (324 mg, 2.0 mmol) and the mixture was stirred at RT overnight. The reaction mixture was heated to ca. 50° C. and a solution of methylamine in THF (2 M, 5.0 mmol) was added. The resulting mixture was stirred at 50° C. overnight and then cooled to RT and diluted with DCM (20 mL). the reaction mixture was washed with sat. NaHCO3 (10 ml) and the organic layer dried (Na2SO4), filtered and concentrated in vacuo. Purification by silica flash column chromatography (eluting with DCM/MeOH 95:5) provided the title compound as off-white solid (140 mg, 41%).

Workup

  1. temperatureThe reaction mixture was heated to ca. 50° C.
  2. stirringThe resulting mixture was stirred at 50° C. overnight
  3. temperaturecooled to RT
  4. washthe reaction mixture was washed with sat. NaHCO3 (10 ml)
  5. dry with materialthe organic layer dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification
  9. washby silica flash column chromatography (eluting with DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-21d232d9658243fc870826e0c7600643
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

Loading…