1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 21916415, compound

HRID 1429714Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:13])[N:4]([CH2:10][CH2:11][CH3:12])[C:5](=[O:9])[NH:6][C:7]=1[NH2:8].[F:14][C:15]([F:32])([F:31])[C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][CH:30]=1)[CH2:19][N:20]1[CH:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[N:21]1.CCN=C=NCCCN(C)C.Cl>CO>[NH2:8][C:7]1[NH:6][C:5](=[O:9])[N:4]([CH2:10][CH2:11][CH3:12])[C:3](=[O:13])[C:2]=1[NH:1][C:25]([C:23]1[CH:22]=[N:21][N:20]([CH2:19][C:18]2[CH:28]=[CH:29][CH:30]=[C:16]([C:15]([F:32])([F:14])[F:31])[CH:17]=2)[CH:24]=1)=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5,6-diamino-3-propyl-1H-pyrimidine-2,4-dione (4.25 g, 0.023 mol), 1-(3-Trifluoromethyl-benzyl)-1H-pyrazole-4-carboxylic acid (6.23 g, 0.023 mol), prepared by conventional methods starting from pyrazole-4-carboxylic ester, in methanol (50 ml) were cooled to 0° C. and added EDCI.HCl (8.82 g, 0.046 mol). The reaction mixture was stirred at 25° C. for 6 h and the organic volatiles were evaporated. To this residue water (50 ml) was added and the precipitate was filtered off, and washed with cold water (50 ml) to obtain 1-(3-Trifluoromethyl-benzyl)-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (7.2 g, 72%) as a pale yellow solid.

Workup

customprepared by conventional methods
customthe organic volatiles were evaporated
additionTo this residue water (50 ml) was added
filtrationthe precipitate was filtered off
washwashed with cold water (50 ml)

Sources & evidence

ORD record: ord-194c76379d0f4cc3aad449cf403c967c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940751B2

Reaction notes

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