Dimethylamine → HCID 66915940, compound

HRID 2356962Notes

Reaction equation

HRID 2356962 reaction equation
[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=[CH:22][CH:21]=4)[C:12]3=[O:30])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.Cl[CH2:33][C:34](Cl)=[O:35].[CH3:37][NH:38][CH3:39]>ClCCCl>[CH3:37][N:38]([CH3:39])[CH2:33][C:34]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N:11]3[C:15](=[O:16])[C:14]([CH3:17])([CH3:18])[N:13]([CH2:19][C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=[CH:22][CH:21]=4)[C:12]3=[O:30])[CH:6]=2)[C:2]([CH3:31])([CH3:1])[CH2:3]1)=[O:35]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6577Chloroacetyl chlorideHCID 11668799HCID 11668799, compound

Product 1

HCID 66915940HCID 66915940, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 50 mg 3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-1-quinolin-4-ylmethyl-imidazolidine-2,4-dione in 1 ml 1,2-dichloroethane 0.04 ml ethyl-diisopropyl-amine and 13.7 mg chloroacetylchloride were added at 0° C. After stirring for 1 hour at 0° C. 5.5 mg dimethyl-amine were added and the reaction mixture was stirred for 2 days at room temperature. After removing of the solvent under reduced pressure the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid). After lyophilization of the solution the resulting crude product was purified in addition by flash chromatography on silica gel with a dichloro-methane/methanol gradient. The fractions containing the product were evaporated to yield a white solid.

Workup

  1. stirringthe reaction mixture was stirred for 2 days at room temperature
  2. customAfter removing of the solvent under reduced pressure the residue
  3. customwas purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
  5. customAfter lyophilization of the solution the resulting crude product was purified in addition by flash chromatography on silica gel with a dichloro-methane/methanol gradient
  6. additionThe fractions containing the product
  7. customwere evaporated
  8. customto yield a white solid

Sources & evidence

ORD record
ord-3c5f24d4debb45f09d266068b0be9936
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

Loading…