Dimethylamine → 2-Chloro-6,N,N-trimethyl-isonicotinamide

HRID 241699

Reaction equation

HRID 241699 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5](O)=[O:6].C[CH2:13][N:14](C(C)C)[CH:15](C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CNC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([N:14]([CH3:15])[CH3:13])=[O:6]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 569668552-Chloro-6,N,N-trimethyl-isonicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Chloro-6-methyl-isonicotinic acid (1 g) in DMF (200 ml) at 25° C. was added DIPEA (2.9 mL) and TBTU (1.8 ml). After 5 min, dimethylamine (0.75 g) was added dropwise. This was stirred overnight. The reaction was added to water and extracted with EtOAc. The organic layer was separated, dried and concentrated in vacuum. Flash chromatography (9:1 to 2:8 gradient cyclohexane:EtOAc) afforded the title compound (320 mg). Rf=0.56 (1:1 cyclohexane:EtOAc)

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-70313f00a4a9493bb6a4f5a3de3d76a6
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Linked notes

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