Dimethylamine → HCID 53310699, compound

HRID 2389923Notes

Reaction equation

HRID 2389923 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]4[O:15][CH2:16][CH2:17][C:11]=4[N:10]3[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][NH:20][CH3:21].[CH2:22]=O>O.C(#N)C>[CH3:19][N:20]([CH3:22])[CH2:21][C:18]1[N:10]2[C:11]3[CH2:17][CH2:16][O:15][C:12]=3[CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 53310698HCID 53310698, compound

Product 1

HCID 53310699HCID 53310699, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

7-Phenyl-1,2-dihydrofuro[2,3-e]imidazo[1,2-a]pyridine (40 mg, 0.169 mol) was dissolved in a mixed solvent of water (400 μL) and acetonitrile (1 mL), 50% aqueous dimethylamine (15.1 mg) solution and 36% aqueous formalin (14.2 mg) solution were added, and the mixture was stirred at 70° C. for 4 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0) to give the title compound (45 mg, 95%).

Workup

  1. additionwere added
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0)

Sources & evidence

ORD record
ord-19a19adfa450468090d58e9774d6782c
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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