4-Fluorobenzohydrazide → HCID 86279413, compound

HRID 576717Notes

Reaction equation

HRID 576717 reaction equation
[Cl:1][C:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]=[C:7](OCC)[C:6]1=[O:15].[F:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=O)=[CH:27][CH:26]=1>C(O)CCC>[Cl:1][C:2]1[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]2[C:29]([C:28]3[CH:33]=[CH:34][C:25]([F:24])=[CH:26][CH:27]=3)=[N:31][N:32]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 99724-FluorobenzohydrazideHCID 90402498HCID 90402498, compound

Product 1

HCID 86279413HCID 86279413, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (6S)-1-(2-chloro-3-(trifluoromethyl)benzyl)-3-ethoxy-6-methyl-5,6-dihydropyrazin-2(1H)-one (216 mg, 0.62 mmol) and 4-fluorobenzohydrazide (105 mg, 0.68 mmol) in 1-butanol (6.2 mL) was heated at 130° C. for 16 h. After cooling to rt, the solvent was removed in vacuo. Purification by chromatography (SiO2; 0-10% IPA/EtOAc) afforded the desired product as a white solid (158 mg, 58%). MS (ESI): mass calcd. for C20H15ClF4N4O, 438.1; m/z found, 439.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.77-7.70 (m, 3H), 7.68-7.59 (m, 1H), 7.38 (t, J=7.8 Hz, 1H), 7.25-7.15 (m, 2H), 5.33 (d, J=15.7 Hz, 1H), 4.66 (dd, J=13.0, 4.5 Hz, 1H), 4.55 (d, J=15.7 Hz, 1H), 4.23 (dd, J=13.0, 2.0 Hz, 1H), 4.11 (dt, J=14.3, 4.8 Hz, 1H), 1.27-1.24 (m, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by chromatography (SiO2; 0-10% IPA/EtOAc)

Sources & evidence

ORD record
ord-ab2ed17623a84908bd3d9d0303dda43d
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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