4-Fluoro-n-hydroxybenzimidamide → HCID 136492494, compound

HRID 508937Notes

Reaction equation

HRID 508937 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]1[NH:24][C:23](=[O:25])[N:22]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#N)=[CH:28][CH:27]=2)[N:21]=1>CN(C=O)C.[Cl-].[Cl-].[Zn+2]>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]1[NH:24][C:23](=[O:25])[N:22]([C:26]2[CH:27]=[CH:28][C:29]([C:30]3[O:9][N:8]=[C:6]([C:5]4[CH:10]=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)[N:7]=3)=[CH:32][CH:33]=2)[N:21]=1

Participants

5

Reactant 2

HCID 5930004-Fluoro-n-hydroxybenzimidamideHCID 136644910HCID 136644910, compound

Product 1

HCID 136492494HCID 136492494, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-fluoro-N′-hydroxybenzimidamide (Intermediate-18, 0.073 g, 0.47 mmol) in dry DMF (3 mL) under nitrogen atmosphere was added 4-(3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzonitrile (step-4 of Intermediate-17, 0.100 g, 0.31 mmol) and ZnCl2 (0.0087 g, 0.06 mmol). The reaction mass was heated at 100° C. for 8-10 h. The reaction mass was quenched with water, extracted in DCM and column purified to afford 0.025 g of desired product. 1HNMR (DMSO-d6): δ 7.02 (br s, 1H), 7.33 (t, 1H), 7.45-7.54 (m, 2H), 7.61 (d, 1H), 7.70 (m, 1H), 7.83 (t, 1H), 8.09-8.17 (m, 2H), 8.26-8.30 (m, 2H), 12.81 (br s, 1H). MS (m/z): 452.05 [M+H]+.

Workup

  1. customThe reaction mass was quenched with water
  2. extractionextracted in DCM
  3. customcolumn purified

Sources & evidence

ORD record
ord-25a2473f2d11423b82dccef24d58ace2
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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