Pyrazine-2-Carboxylic Acid Hydrazide → HCID 86279877, compound

HRID 576721Notes

Reaction equation

HRID 576721 reaction equation
[Cl:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][N:8]=[C:7](OC)[C:6]1=[O:16].[N:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[C:31]([NH:33][NH2:34])=O>C(O)CCC>[Cl:1][C:2]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][N:8]2[C:31]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][N:25]=3)=[N:33][N:34]=[C:7]2[C:6]1=[O:16]

Participants

4

Reactant 2

HCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 90402452(+/-)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-methoxy-5,6-dihydropyrazin-2(1H)-one

Product 1

HCID 86279877HCID 86279877, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (±)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-methoxy-5,6-dihydropyrazin-2(1H)-one (216 mg, 0.58 mmol) and pyrazine-2-carbohydrazide (88 mg, 0.63 mmol) in 1-butanol (5.8 mL) was heated at 130° C. for 16 h. After cooling to rt, the solvent was removed in vacuo. Purification by chromatography (SiO2; hexanes—100% EtOAc) afforded the desired product as a white solid (116 mg, 45%). MS (ESI): mass calcd. for C20H16ClF3N6O, 448.1; m/z found, 449.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.69-9.58 (m, 1H), 8.70 (d, J=2.6 Hz, 1H), 8.64 (dd, J=2.5, 1.5 Hz, 1H), 7.75-7.62 (m, 2H), 7.38 (t, J=7.8 Hz, 1H), 5.49 (d, J=15.9 Hz, 1H), 5.27-5.16 (m, 1H), 4.78 (dd, J=15.6, 1.7 Hz, 1H), 4.68 (ddd, J=13.9, 4.5, 2.4 Hz, 1H), 3.16 (ddd, J=9.9, 4.5, 3.3 Hz, 1H), 1.06-0.96 (m, 1H), 0.80-0.72 (m, 1H), 0.67-0.43 (m, 2H), 0.28-0.21 (m, 1H).

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by chromatography (SiO2; hexanes—100% EtOAc)

Sources & evidence

ORD record
ord-3db7068aa26e455185b468f600a6d385
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

Loading…