Methylamine → 7-methoxy-N,2-dimethylimidazo[1,2-a]pyridine-3-carboxamide

HRID 130668Notes

Reaction equation

HRID 130668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([OH:15])=O)=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1.C[CH2:17][N:18]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CN>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:13]([NH:18][CH3:17])=[O:15])=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534853377-Methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 860551557-methoxy-N,2-dimethylimidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-methoxy-2-methylimidazo[1,2-α]pyridine-3-carboxylic acid (1.2 g, 5.82 mmol) in DMF (25 ml) was added EDCl (1.23 g, 6.41 mmol), HOBt (0.87 g, 6.41 mmol), N-methyl morpholine (767 ul, 11.64 mmol), methylamine (2M in THF, 6 ml, 11.64 mmol) and DMAP (70 mg, 0.58 mmol) sequentially, and the resulting mixture stirred at ambient temperature for 16 hours. The resulting solution was concentrated in-vacuo and pre-absorbed onto SiO2 and then purified by flash chromatography (eluting with 5-8% MeOH/DCM) to yield 7-Methoxy-N,2-dimethylimidazo[1,2-α]pyridine-3-carboxamide, 1.11 g, 87%, as a white solid.

Workup

  1. concentrationThe resulting solution was concentrated in-vacuo
  2. custompre-absorbed onto SiO2
  3. custompurified by flash chromatography (eluting with 5-8% MeOH/DCM)

Sources & evidence

ORD record
ord-4423f8afff4b4118a05ea6e3aabe6fb0
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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