Pyridine → HCID 22672618, compound

HRID 1006675Notes

Reaction equation

HRID 1006675 reaction equation
[NH2:1][CH2:2][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1.N1C=CC=CC=1.Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl>[CH3:16][C:14]1[N:15]=[C:8]2[C:7]([NH:6][CH2:5][C:4]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:3]=3[CH2:2][NH:1][C:30](=[O:31])[O:32][CH3:33])=[CH:12][CH:11]=[CH:10][N:9]2[C:13]=1[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 22672573HCID 22672573, compound

Product 1

HCID 22672618HCID 22672618, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12 °C

Procedure

To an ice cooled solution of 8-(2-aminomethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.17 g, 0.58 mmol), pyridine (0.046 g, 0.58 mmol) in methylene chloride (8 ml) was added methyl chloroformate (0.055 g, 0.58 mmol) and the reaction mixture was stirred for 1.5 h. and the temperature was allowed to raise to 12° C. Methylene chloride was added and the solution was washed twice with water. The organic layer was separated, washed with saturated sodium bicarbonate, dried and evaporated under reduced pressure. The residue was purified by by column chromatography on silica gel using methylene chloride:methanol (100:5) as eluent. Recrystallization from diethyl ether gave 0.052 g (25%) of the title compound.

Workup

  1. washthe solution was washed twice with water
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by by column chromatography on silica gel
  7. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-6f18b423e5544023964dd2a268ece7c5
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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