2-(Dimethylamino)ethanol → HCID 22405173, compound

HRID 441252Notes

Reaction equation

HRID 441252 reaction equation
[C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:39])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:38])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:19][CH:18]=2)[CH2:8][CH2:7][C:6]1=[O:40])([OH:3])=[O:2].[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44]O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44][O:2][C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:39])[C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:38])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:21][CH:22]=2)[CH2:8][CH2:7][C:6]1=[O:40])=[O:3]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 10868DicyclohexylcarbodiimideHCID 10506457HCID 10506457, compound

Product 1

HCID 22405173HCID 22405173, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-carboxymethyl-5-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (220 mg), 2-dimethylaminoethanol (37 mg) and 4-dimethylaminopyridine (10 mg) in dichloromethane (5 ml) were added dicyclohexylcarbodiimide (102 mg) at ambient temperature and the mixture was stirred at the same temperature for 30 hours. The resulting mixture was washed with saturated sodium bicarbonate aqueous solution. Drying over magnesium sulfate, filtering and the removal of solvents afforded a crude product. The crude product was purified by silica gel column (3% methanol in chloroform). The solvent was evaporated in vacuo and the residue was solidified with diethyl ether to give 1-[(2-dimethylaminoethoxy)carbonylmethyl]-5-{4-[2-(2-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (86 mg) as a white powder.

Workup

  1. washThe resulting mixture was washed with saturated sodium bicarbonate aqueous solution
  2. dry with materialDrying over magnesium sulfate
  3. filtrationfiltering
  4. customthe removal of solvents
  5. customafforded a crude product
  6. customThe crude product was purified by silica gel column (3% methanol in chloroform)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ab09ca17288c4c21b5a6f5973f7435e8
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

Loading…