1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22267481, compound

HRID 2217166Notes

Reaction equation

HRID 2217166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH2:15][C:16]([OH:18])=O)[C:11](=[O:19])[CH:10]=[N:9]2)=[CH:4][C:3]=1[C:20](=[O:31])[NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30].Cl.CN.C[CH2:36][N:37]=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH2:15][C:16](=[O:18])[NH:37][CH3:36])[C:11](=[O:19])[CH:10]=[N:9]2)=[CH:4][C:3]=1[C:20]([NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])=[O:31]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6364545Methylamine hydrochlorideHCID 68656783HCID 68656783, compound

Product 1

HCID 22267481HCID 22267481, compoundYield 27.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A slurry of (2-{4-Chloro-3-[2-(2-chloro-phenyl)-ethylcarbamoyl]-phenyl}-3,5-dioxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-acetic acid (71.4 mg, 0.154 mmol), methylamine HCl (15.6 mg, 0.231 mmol), EDCI (44.4 mg, 0.231 mmol), and DMAP (75.5 mg, 0.616 mmol) in DMF (1.0 mL) were stirred at ambient temperature for 20 hours. The reaction was diluted with 1N HCl, and let stir for 5 hours. The crude was filtered and triterated from hexane to give the title compound (20 mg). LCMS (m/z) 476.1 M+1.

Workup

  1. filtrationThe crude was filtered

Sources & evidence

ORD record
ord-5214685cf6ec49289a1ce6051336a820
Source dataset
uspto-grants-2008_08
Patent number
US07407956B2

Reaction notes

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