HCID 21090617, compound → HCID 21090623, compound

HRID 350961Notes

Reaction equation

HRID 350961 reaction equation
[CH:1]([N:4]=[C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:8](=[O:17])[CH:7]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[S:6]1)([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH:7]2[S:6][C:5](=[N:4][CH:1]([CH3:3])[CH3:2])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:8]2=[O:17])=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 21090617HCID 21090617, compound

Product 1

HCID 21090623HCID 21090623, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-isopropylimino-5-(4-nitrophenyl)-3-pyridin-2-ylmethyl-thiazolidin-4-one (4.6 g, 12.4 mmol) in dry methanol (50 ml) was subjected to hydrogenation at slightly above atmospheric pressure (balloon) room temperature for 20 h using Pearlman's catalyst (1.0 g). After 20 h at room temperature, additional catalyst (0.5 g) was added and the suspension was hydrogenated for an additional 24 h. When the reaction was judged complete by LC analysis, the mixture was suction-filtered through Celite and concentrated in vacuo to afford the title compound as a yellowish-tan foam which was used without further purification: 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=4.2 Hz, 1H), 7.61–7.57 (m, 1H), 7.21–7.16 (m, 1H), 7.18 (d, J=8.3 Hz, 2H), 7.14–7.12 (m, 1H), 6.63 (d, J=8.6 Hz, 2H), 5.15 (s, 1H), 5.08 (s, 2H), 3.85–3.60 (br m, 2H), 3.50–3.42 (m, 1H), 1.09–1.06 (m, 6H); MS (ESI) m/z=341.2 (MH+); HPLC rt 1.07 min. (3 min. grad.); Purity (83.5%).

Workup

  1. waitthe suspension was hydrogenated for an additional 24 h
  2. filtrationthe mixture was suction-filtered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79a6e9862c7b4d2ba63dbafbf668ef33
Source dataset
uspto-grants-2007_02
Patent number
US07183302B2

Reaction notes

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