1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → n-(6-Amino-1-ethyl-2,4-dioxo(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl} pyrazol-4-yl)carboxamide

HRID 1713191

Reaction equation

HRID 1713191 reaction equation
[NH2:1][C:2]1[C:3](=[O:12])[NH:4][C:5](=[O:11])[N:6]([CH2:9][CH3:10])[C:7]=1[NH2:8].[F:13][C:14]([F:31])([F:30])[C:15]1[CH:16]=[C:17]([CH2:21][N:22]2[CH:26]=[C:25]([C:27](O)=[O:28])[CH:24]=[N:23]2)[CH:18]=[CH:19][CH:20]=1.Cl.CN(C)CCCN=C=NCC>CO>[NH2:8][C:7]1[N:6]([CH2:9][CH3:10])[C:5](=[O:11])[NH:4][C:3](=[O:12])[C:2]=1[NH:1][C:27]([C:25]1[CH:24]=[N:23][N:22]([CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:31])([F:13])[F:30])[CH:16]=2)[CH:26]=1)=[O:28]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114927411-(3-(Trifluoromethyl)benzyl)-1H-pyrazole-4-carboxylic acidHCID 219163605,6-Diamino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 21916363n-(6-Amino-1-ethyl-2,4-dioxo(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl} pyrazol-4-yl)carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5,6-diamino-1-ethyl-1,3-dihydropyrimidine-2,4-dione (2 g, 11.76 mmol) and 1-{[3-(trifluoromethyl)phenyl]methyl}pyrazole-4-carboxylic acid (3.5 g, 12.94 mmol) in methanol (50 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.47 g, 12.94 mmol), and the reaction mixture was stirred for 16 hours at room temperature. Solvent was removed under reduced pressure, and the residue was washed with water and methanol. The product was dried under vacuum to provide N-(6-amino-1-ethyl-2,4-dioxo(1,3-dihydropyrimidin-5-yl))(1-{[3-(trifluoromethyl)phenyl]methyl}pyrazol-4-yl)carboxamide, a compound of formula (16).

Workup

  1. customSolvent was removed under reduced pressure
  2. washthe residue was washed with water and methanol
  3. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-4d7de872bf9849b2adf6f93de4a76121
Source dataset
uspto-grants-2010_09
Patent number
US07795268B2

Linked notes

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