Dimethylamine → HCID 178484549, compound

HRID 1170459Notes

Reaction equation

HRID 1170459 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:22])[C:9](=[CH:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)[C:10](O)=[O:11].[CH:23]1([N:29]=[C:30]=NC2CCCCC2)CCCCC1.CNC>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:22])[C:9](=[CH:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)[C:10]([N:29]([CH3:30])[CH3:23])=[O:11]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 178525594HCID 178525594, compound

Product 1

HCID 178484549HCID 178484549, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-chloro-α-[[(4-iodophenyl)amino]methylene]-β-oxobenzenepropanoic acid (43 mg, 0.10 mmol) in 1 mL of CH2Cl2 was added N,N′-dicyclohexylcarbodiimide (21 mg, 0.10 mmol). The mixture was cooled in an ice bath and 50 μL (0.10 mmol) of a 2M solution of dimethylamine in THF was added. The reaction mixture was stirred at rt for 16 h. The formed DCU was removed by filtration. The filtrate was washed with water and evaporated to dryness. The title compound (22 mg, 50%) was isolated by column chromatography (5% MeOH in CH2Cl2); MS 410 (M−45), 455(M+1), 477(M+Na+).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe formed DCU was removed by filtration
  3. washThe filtrate was washed with water
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5cbb1fe7caf846518f4e4b5c4302f75c
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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