Nicotinic acid, hydrazide → HCID 86279547, compound

HRID 576719Notes

Reaction equation

HRID 576719 reaction equation
[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][NH:8][C:7](=S)[C:6]1=[O:13].[C:22]([NH:30][NH2:31])(=O)[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1>C(O)CCC>[Cl:1][C:2]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]2[C:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[N:30][N:31]=[C:7]2[C:6]1=[O:13]

Participants

4

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 90402242HCID 90402242, compound

Product 1

HCID 86279547HCID 86279547, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (S)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-methyl-3-thioxopiperazin-2-one (105 mg, 0.31 mmol) and nicotinohydrazide (47 mg, 0.34 mmol) in 1-butanol (3.1 mL) was heated at 130° C. for 16 h. After cooling to rt, the solvent was removed in vacuo. Purification by chromatography (SiO2; 0-20% IPA/EtOAc) afforded the desired product as a white solid (102 mg, 78%). MS (ESI): mass calcd. for C19H15ClF3N5O, 421.1; m/z found, 422.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.90 (d, J=1.8 Hz, 1H), 8.74 (dd, J=4.8, 1.4 Hz, 1H), 8.16-8.12 (m, 1H), 7.75 (d, J=7.7 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.48 (dd, J=7.9, 4.9 Hz, 1H), 7.39 (t, J=7.8 Hz, 1H), 5.35 (d, J=15.6 Hz, 1H), 4.68 (dd, J=12.9, 4.5 Hz, 1H), 4.57 (d, J=15.6 Hz, 1H), 4.25 (dd, J=12.9, 1.8 Hz, 1H), 4.19-4.09 (m, 1H), 1.30 (d, J=6.7 Hz, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by chromatography (SiO2; 0-20% IPA/EtOAc)

Sources & evidence

ORD record
ord-ab7d78f6b58c4067a00e56af6df0cc74
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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