Triethylamine → N,N-Dimethyl-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridin-2-amine

HRID 627489Notes

Reaction equation

HRID 627489 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)=[O:9])=[CH:4][N:3]=1.Cl.[CH3:17][NH:18][CH3:19].CCN(CC)CC>CO>[CH3:17][N:18]([CH3:19])[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 120166732-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine2×

Product 1

HCID 86716071N,N-Dimethyl-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

In a 50-mL round-bottom flask was placed a solution of 2-chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine (250 mg, 1.13 mmol, Intermediate 22, step c), dimethylamine hydrochloride (96 mg, 1.2 mmol), and Et3N (342 mg, 3.39 mmol) in methanol (15 mL). The resulting mixture was heated at 75° C. overnight and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel column, 100:0-20:1 CH2Cl2/MeOH) to give the title compound as a light yellow solid.

Workup

  1. customIn a 50-mL round-bottom flask was placed
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash column chromatography (silica gel column, 100:0-20:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-e7ec708e8e7440d5af384e792da973a2
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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