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

HRID 488718Notes

Reaction equation

HRID 488718 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-cf69facee85d4d25889d88a6bac3c4a7
Source dataset
uspto-grants-2005_12
Patent number
US06974812B2

Reaction notes

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