Chloroacetyl chloride → HCID 11671104, compound

HRID 2356951Notes

Reaction equation

HRID 2356951 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].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>ClCCCl>[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]([CH3:17])([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:8][CH:9]=2)[N:4]([C:34](=[O:35])[CH2:33][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:3]1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8083Morpholine2×HCID 11668799HCID 11668799, compound

Product 1

HCID 11671104HCID 11671104, 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-diisopropylamine and 13.67 mg chloroacetylchloride were added at 0° C. After stirring for 1 hour at 0° C. 10.5 mg morpholine were added and the reaction mixture was stirred for 1 hour at room temperature. Then 10.5 mg morpholine were added and the mixture was stirred for further 16 hours 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). Lyophilization of the solution yielded a white solid.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour at room temperature
  2. stirringthe mixture was stirred for further 16 hours at room temperature
  3. customAfter removing of the solvent under reduced pressure the residue
  4. customwas purified by preparative HPLC (
  5. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
  6. customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record
ord-b51d2756578040448ecfd60a166713b2
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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