Pyridine → HCID 15684587, compound

HRID 728150Notes

Reaction equation

HRID 728150 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]4[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]4[CH:26]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([NH:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]4[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]4[CH:26]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 15684552HCID 15684552, compound

Product 1

HCID 15684587HCID 15684587, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of acetyl chloride (1.94 g) in dichloromethane (6 ml) was added dropwise to a solution of 2-amino-6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (6.00 g) and pyridine (4.92 ml) in dichloromethane (60 ml) with stirring at 0° C. The mixture was stirred for two hours at the same temperature and further 22 hours at ambient temperature. Saturated aqueous sodium hydrogen carbonate solution (100 ml) was added thereto and that was stirred for 2.5 hours at 0° C. The resulting precipitate was collected by filtration and washed with water. Recrystallization from a mixture of ethanol and diethyl ether gave 2-acetylamino-6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (4.00 g).

Workup

  1. stirringThe mixture was stirred for two hours at the same temperature and further 22 hours at ambient temperature
  2. stirringthat was stirred for 2.5 hours at 0° C
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customRecrystallization
  6. additionfrom a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-ac1bd6f9595a4bd2b169cf87f63e5a8b
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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