N,N-Dimethylethylenediamine → HCID 69156431, compound

HRID 750293Notes

Reaction equation

HRID 750293 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21](O)=[O:22])[CH:16]=1)=[CH:12][C:11]([Cl:24])=[CH:10][CH:9]=2)=[O:4].[CH3:37][N:38]([CH3:42])[CH2:39][CH2:40][NH2:41].Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21](=[O:22])[NH:41][CH2:40][CH2:39][N:38]([CH3:42])[CH3:37])[CH:16]=1)=[CH:12][C:11]([Cl:24])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69156399HCID 69156399, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 69156431HCID 69156431, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution (2 ml) of 4-(3-carboxyphenyl)-6-chloro-2-(4-methanesulfonylbenzyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (100 mg) and N,N-dimethylethylenediamine (23 μl) in acetonitrile were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (69 mg) and 4-hydroxybenzotriazole monohydrate (38 mg) at room temperature with stirring, and the mixture was stirred at room temperature for 12 hrs. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was dried and concentrated to dryness. The residue was purified by silica gel column chromatography (dichloromethane/methanol=10/1) to give the title compound (56 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hrs
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. customThe organic layer was dried
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-f8a8df2f8faa4a8d93eda40637e9e465
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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