Dimethylamine → HCID 18923350, compound

HRID 1290202Notes

Reaction equation

HRID 1290202 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[C:13]2[N:14]([C:18]([Cl:22])=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1)[CH3:6])=[O:4].[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)[CH3:29].BrCC(Cl)=[O:38].CNC>ClCCl>[Cl:22][C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[C:23]([Cl:26])=[CH:24][CH:25]=[C:7]([N:5]([C:3](=[O:4])[CH2:2][NH:1][C:29](=[O:38])[CH2:28][N:30]([CH3:33])[CH3:31])[CH3:6])[C:8]=3[Cl:27])[C:13]2=[N:20][C:19]=1[CH3:21]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 18923650HCID 18923650, compound

Product 1

HCID 18923350HCID 18923350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-3-chloro-2-methylimidazo[1,2-a]pyridine (200 mg), triethylamine (0.1 ml) and dichloromethane (2 ml) was added bromoacetyl chloride (0.042 ml) in a dry ice-acetone bath. After 20 minutes, to the mixture was added 50% aqueous solution of dimethylamine (0.42 ml). The mixture was stirred for 1 hour at ambient temperature. The reaction mixture was washed with aqueous sodium bicarbonate solution, water and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography (dichloromethane:methanol=20:1, V/V) to yield colorless crystals (191 mg) of 3-chloro-8-[2,6-dichloro-3-[N-[N-(N,N-dimethylglycyl)glycyl]-N-methylamino]benzyloxy]-2-methylimidazo[1,2-a]pyridine.

Workup

  1. washThe reaction mixture was washed with aqueous sodium bicarbonate solution, water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (dichloromethane:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-83cd982916774eccbc85921f531be391
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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