Dimethylamine → 1-(2-chloropyridin-4-ylmethyl)-3-[1-(2-dimethylamino-acetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-imidazolidine-2,4-dione

HRID 546608

Reaction equation

HRID 546608 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:14]3[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[N:16]([CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[CH:24]=4)[C:15]3=[O:30])[CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6]1)=[O:4].[CH3:33][NH:34][CH3:35]>O1CCCC1>[Cl:29][C:25]1[CH:24]=[C:23]([CH2:22][N:16]2[C:17]([CH3:21])([CH3:20])[C:18](=[O:19])[N:14]([C:11]3[CH:12]=[C:13]4[C:8]([C:7]([CH3:31])([CH3:32])[CH2:6][N:5]4[C:3](=[O:4])[CH2:2][N:34]([CH3:35])[CH3:33])=[CH:9][CH:10]=3)[C:15]2=[O:30])[CH:28]=[CH:27][N:26]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 576259893-[1-(chloroacetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 576260011-(2-chloropyridin-4-ylmethyl)-3-[1-(2-dimethylamino-acetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.951 g of 3-[1-(chloroacetyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage j) of Example 3 in 80 mL of a 2M solution of dimethylamine in tetrahydrofuran is heated at 60° C. for 4 hours. The reaction mixture is then concentrated under reduced pressure and is triturated in 30 mL of water. A solid forms, which is filtered off, washed with twice 5 mL of diisopropyl ether and dried to give 3.5 g of 1-[(2-chloropyridin-4-yl)methyl]-3-[1-(N,N-dimethylglycyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows:

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. customis triturated in 30 mL of water
  3. filtrationA solid forms, which is filtered off
  4. washwashed with twice 5 mL of diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-1b469954a8d649e6ba5941575cb0a7f4
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Linked notes

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