Nicotinic acid, hydrazide → HCID 86279944, compound

HRID 576723Notes

Reaction equation

HRID 576723 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[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][NH:8][C:7](=S)[C:6]1=[O:15].[C:24]([NH:32][NH2:33])(=O)[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=1>C(O)CCC>[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[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][N:8]2[C:24]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[N:32][N:33]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 90402344HCID 90402344, compound

Product 1

HCID 86279944HCID 86279944, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (±)-1-(2-chloro-3-(trifluoromethyl)benzyl)-6-cyclopropyl-3-thioxopiperazin-2-one (100 mg, 0.28 mmol) and nicotinohydrazide (38 mg, 0.28 mmol) in 1-butanol (3 mL) was heated at 130° C. for 16 h. After cooling to rt, the precipitate was filtered and washed with hexanes to afford the desired product as a white solid (68 mg, 55%). MS (ESI): mass calcd. for C21H17ClF3N5O, 447.1; m/z found, 448.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.93 (d, J=1.7 Hz, 1H), 8.79 (dd, J=4.8, 1.6 Hz, 1H), 8.21-8.16 (m, 1H), 7.74-7.61 (m, 2H), 7.52 (dd, J=7.9, 4.9 Hz, 1H), 7.38 (t, J=7.8 Hz, 1H), 5.47 (d, J=15.8 Hz, 1H), 4.76 (d, J=15.8 Hz, 1H), 4.52 (dd, J=12.7, 4.3 Hz, 1H), 4.41 (dd, J=12.7, 3.1 Hz, 1H), 3.18-3.11 (m, 1H), 1.08-0.90 (m, 1H), 0.84-0.69 (m, 1H), 0.59-0.47 (m, 2H), 0.20-0.14 (m, 1H).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with hexanes

Sources & evidence

ORD record
ord-937d4b6495ad492fb3edffc4f856ba67
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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