1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178523899, compound

HRID 2280401Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C:9](=S)[NH:10][C:11]2[NH:15][N:14]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:12]=2)=[O:7])=[CH:4][CH:3]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([F:33])[C:31]=1[F:32])[CH2:27][NH2:28].Cl.C(N=C=NCCCN(C)C)C>CO>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6](/[N:8]=[C:9](/[NH:28][CH2:27][C:26]2[CH:29]=[C:30]([F:33])[C:31]([F:32])=[C:24]([F:23])[CH:25]=2)\[NH:10][C:11]2[NH:15][N:14]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:12]=2)=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Chloro-N-((3-(trifluoromethyl)-1H-pyrazol-5-yl)carbamothioyl)benzamide (500 mg, 1.43 mmol) was dissolved in methanol (5 mL) and 3,4,5-trifluorobenzylamine (462 mg, 2.87 mmol) was added followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (550 mg, 2.87 mmol). The reaction was stirred at 50° C. for 30 minutes. The crude mixture was then partitioned between water and ethyl acetate. The organic layer was washed with brine, and dried over sodium sulfate, then purified by chromatography (gradient: 95:5 hexanes:EtOAc to 7:3 hexanes:EtOAc). (Z)-4-Chloro-N-(((3,4,5-trifluorobenzyl)amino)((3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)methylene)benzamide was obtained as a solid (221 mg, 32% yield). MS (ES+) 475.8.

Workup

customThe crude mixture was then partitioned between water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
custompurified by chromatography (gradient: 95:5 hexanes:EtOAc to 7:3 hexanes:EtOAc)

Sources & evidence

ORD record: ord-e7ef63fed2c04d0cbbbec1904c2f87c9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139532B2

Reaction notes

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