Hydrochloric Acid → HCID 22914804, compound

HRID 1377472Notes

Reaction equation

HRID 1377472 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]2[N:6]([C:10]([CH:14]=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:16][O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Br)=[O:19].Cl>O1CCCC1>[CH:14]([C:10]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:4]([NH:3][CH2:23][C:22]3[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:21]=3[NH:20][C:18]([O:17][CH3:16])=[O:19])[C:5]2=[N:12][C:11]=1[CH3:13])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 21873989HCID 21873989, compoundHCID 22914806HCID 22914806, compound

Product 1

HCID 22914804HCID 22914804, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

A suspension of 400 mg of commercial 80% sodium hydride in 10 ml of dry tetrahydrofuran is added to a solution of 2 g of 8-amino-3-formyl-2-methylimidazo[1,2-a]pyridine in 40 ml of dry tetrahydrofuran at RT. Brief heating at 50° C. is followed by vigorous evolution of gas. After the evolution of gas is complete, the mixture is cooled to 0° C., and a solution of 3.9 g of 2-methoxycarbonylamino-6-methylbenzyl bromide in 40 ml of dry tetrahydrofuran is added dropwise. The mixture is again heated to 50° C. and kept at this temperature for 3 h. It is then poured into ice-water, neutralized with a little dilute hydrochloric acid and extracted four times with ethyl acetate. The collected organic phases are washed with water and dried over sodium sulfate. The solvent is stripped off in vacuo, and the dark brown viscous residue is chromatographed on silica gel (ethyl acetate:petroleum ether=1:1 as eluent). Recrystallization from isopropanol results in 2.5 g of the title compound of m.p. 188°-190° C. (dec.).

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. temperatureThe mixture is again heated to 50° C.
  3. extractionextracted four times with ethyl acetate
  4. washThe collected organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe dark brown viscous residue is chromatographed on silica gel (ethyl acetate:petroleum ether=1:1 as eluent)
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-593db2dfdcae492385ae4f275d513dc7
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

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