Chloroacetyl chloride → HCID 66915778, compound

HRID 2356964Notes

Reaction equation

HRID 2356964 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.C(N(C(C)C)C(C)C)C.Cl[CH2:42][C:43](Cl)=[O:44].[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]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:43](=[O:44])[CH2:42][N:50]2[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]2)[CH2:3]1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 11668799HCID 11668799, compound

Product 1

HCID 66915778HCID 66915778, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 70 mg 3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-1-quinolin-4-ylmethyl-imidazolidine-2,4-dione in 2 ml 1,2-dichloroethane in a process vial 0.06 ml ethyl-diisopropyl-amine and 13.5 mg chloroacetylchloride were added at 0° C. After stirring for 1 hour at 0° C. 33.9 mg 1-methyl-piperazine were added. The resulting mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoracetic acid). Lyophilization of the solution yielded a white solid.

Workup

  1. stirringThe resulting mixture was stirred for 2 hours at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoracetic acid)
  5. customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record
ord-03e29a8c1280425a9823b0607bdab4d3
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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