Triethylamine → N3-[4-(3-Diethylamino-propoxy)-3,5-dimethoxy-phenyl]-1-(2-fluorophenyl)-1H-[1,2,4]triazole-3,5-diamine

HRID 1179248Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].C(N(CC)CC)C.[C:18]([NH:20][C:21](=[N:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH2:39][CH2:40][CH2:41][N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])=[C:32]([O:47][CH3:48])[CH:31]=1)OC1C=CC=CC=1)#[N:19].FC(F)(F)C(O)=O.C(N(CC)CC)C>CC(N(C)C)=O>[CH2:45]([N:42]([CH2:43][CH3:44])[CH2:41][CH2:40][CH2:39][O:38][C:33]1[C:32]([O:47][CH3:48])=[CH:31][C:30]([NH:29][C:21]2[N:20]=[C:18]([NH2:19])[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[F:2])[N:10]=2)=[CH:35][C:34]=1[O:36][CH3:37])[CH3:46]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 2-fluoro-phenylhydrazine hydrochloride (0.15 g, 0.91 mmol) and triethylamine (0.13 mL, 0.91 mmol) in dimethylacetaimde (1 mL) was stirred 0.5 h at room temperature. N-cyano-N′-(4-(3-diethylamino-propoxy)-3,5-dimethoxy-phenyl)-O-phenylisourea (0.30 g as a mixture with triethylamine-trifluoroacetic acid salt, 0.45 mmol) in dimethylacetamide (1 mL) was added and the reaction was stirred at 120° C. for 20 h. The precipitate was removed and the filtrate was washed with ether. The remaining aqueous phase was evaporated and was purified by semi-preparative HPLC to provide the title compound (0.01 g, 4% yield) as a yellow lyophilate.

Workup

customThe precipitate was removed
washthe filtrate was washed with ether
customThe remaining aqueous phase was evaporated
customwas purified by semi-preparative HPLC

Sources & evidence

ORD record: ord-4e56eee0ba704b4584e8928d740ecde6
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279469B2

Reaction notes

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