Triethylamine → HCID 22112924, compound

HRID 726305Notes

Reaction equation

HRID 726305 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[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[CH:17]2)[CH3:6])=[O:4].C(N(CC)CC)C.Br[CH2:36][C:37](Cl)=[O:38].[CH3:40][NH:41][CH:42]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[CH:42]1([N:41]([CH3:40])[CH2:36][C:37]([NH:1][CH2:2][C:3]([N:5]([C:7]2[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:10][O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[C:19]([CH3:22])[CH:18]=[CH:17]3)[CH3:6])=[O:4])=[O:38])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 276275N-cycloheptyl-N-methylamineHCID 117954848-[3-(N-glycyl-N-methylamino)2,6-dichlorobenzyloxy]-2-methylquinoline

Product 1

HCID 22112924HCID 22112924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (150 ml), triethylamine (0.077 ml) and dichloromethane (1.5 ml) was added bromoacetyl chloride (0.034 ml) in a dry ice-acetone bath. After 30 minutes, to the mixture was added N-methyl-N-cycloheptylamine (236 mg). The mixture was stirred for 3 hours 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) to yield 8-[3-[N-[(N-cycloheptyl-N-methylglycyl)glycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (151 mg) as amorphous.

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)

Sources & evidence

ORD record
ord-e05f47152bb24722be7ccfae9bc214f9
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

Loading…