4-Fluorobenzoyl chloride → N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-fluorobenzoyl]amino]-benzamide monohydrochloride

HRID 1608825Notes

Reaction equation

HRID 1608825 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:25])=[O:24])=[CH:21][CH:20]=1>>[ClH:25].[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085562N-[2-(1H-Imidazol-2-yl)ethyl]-2-[[4-fluorobenzoyl]amino]-benzamide monohydrochloride

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 2.00 g (0.00869 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 2.81 g 0.01738 mol) of p-fluorobenzoyl chloride with the exception that separation of the aqueous and organic layers provided an aqueous slurry containing the desired product. This slurry was filtered and the solid obtained thereby was washed with ethyl acetate to provide 1.17 g of a solid. The filtrate was then reduced to dryness under reduced pressure to provide an additional 2.0 g of a solid. The solids were combined and then dissolved in methanol containing diethyl ether and hydrochloric acid and the resulting solution was reduced to dryness under reduced pressure. The final product was purified by crystallization from a cyanomethane/methanol solution followed by recrystallization from an ethanol/diethyl ether solution to provide 2.75 g of the desired titled compound (m.p. 209°-210° C.). Analysis for C19H17FN4O2.HCl: Calc.: C, 58.69; H, 4.67; N, 14.41; Found: C, 58.60; H, 4.80; N, 14.18.

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customthat separation of the aqueous and organic layers
  3. customprovided an aqueous slurry
  4. filtrationThis slurry was filtered
  5. customthe solid obtained
  6. washthereby was washed with ethyl acetate

Sources & evidence

ORD record
ord-f63eaa699e0b4969acea129815ed5388
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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