Chloroacetyl chloride → HCID 66915947, compound

HRID 2356963Notes

Reaction equation

HRID 2356963 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].[F:46][C:47]([F:51])([F:50])[CH2:48][NH2:49]>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][NH:49][CH2:48][C:47]([F:51])([F:50])[F:46])[CH2:3]1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 9773Ethanamine, 2,2,2-trifluoro-2×HCID 81531DiisopropylethylamineHCID 11668799HCID 11668799, compound

Product 1

HCID 66915947HCID 66915947, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 100 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 0.08 ml ethyl-diisopropyl-amine and 27.2 mg chloroacetylchloride were added at 0° C. After stirring for 1 hour at 0° C. 119.4 mg 2,2,2-trifluoro-ethylamine were added. The resulting mixture was stirred for 1 hour at room temperature and then further 119.4 mg 2,2,2-trifluoro-ethylamine were added. The vial was sealed with a teflon septum and placed in the microwave cavity. The reaction mixture was stirred for 15 minutes at 100° C. by microwave-assisted heating (Emrys Optimizer, Personal Chemistry). After further 15 minutes stirring at 150° C. the solution was heated for 1 hour at 150° C. 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 1 hour at room temperature
  2. stirringThe reaction mixture was stirred for 15 minutes at 100° C.
  3. temperatureby microwave-assisted heating (Emrys Optimizer, Personal Chemistry)
  4. stirringAfter further 15 minutes stirring at 150° C. the solution
  5. temperaturewas heated for 1 hour at 150° C
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by preparative HPLC (
  8. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoracetic acid)
  9. customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record
ord-4cdfad78c13a45d1b5e4a68ec1be481a
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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