Hydrochloric Acid → 1-[N-(2,6-Dibromo-4-fluoro-phenyl)-carbamimidoyl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 408756Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[NH:10][C:11]#[N:12].[NH:13]1[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[N:14]1.Cl.O1CCOCC1>CCOCC>[CH2:21]([O:20][C:18]([C:16]1[CH:17]=[N:13][N:14]([C:11](=[NH:12])[NH:10][C:3]2[C:4]([Br:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Br:1])[CH:15]=1)=[O:19])[CH3:22]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 2,6-dibromo-4-fluoro-phenyl-cyanamide (0.167 g, 0.570 mmol), ethyl pyrazole-4-carboxylate (80.0 mg, 0.570 mmol), 4M HCl in dioxane (0.156 mL, 0.630 mmol), and 1,4 dioxane (2 mL) was heated to reflux for 2 h, during which time a precipitate formed. The mixture was allowed to cool to 23° C. Et2O (10 mL) was added to the mixture. The resulting precipitate was collected by filtration, washed with Et2O, and dried to yield the titled compound (0.134 g, 50%) as the HCl salt. MS (ESI/CI): mass calcd. for C13H11Br2FN4O2, 431.9; m/z found, 432.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.20 (s, 1H), 7.43 (s, 1H), 6.82 (d, J=7.9 Hz, 2H), 3.56 (q, J=7.1 Hz, 2H), 2.85 (s, 3H), 0.57 (t, J=7.1 Hz, 3H).

Workup

temperaturewas heated
temperatureto reflux for 2 h, during which time a precipitate
customformed
filtrationThe resulting precipitate was collected by filtration
washwashed with Et2O
customdried

Sources & evidence

ORD record: ord-1ed4a1627ed147b59f3ef2aaaafc473d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759345B2

Reaction notes

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