Sodium Dithionite → HCID 178434000, compound

HRID 63589Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:26][N:27]1[CH:31]=[C:30]([CH:32]=O)[C:29]([CH3:34])=[N:28]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:32]([C:30]3[C:29]([CH3:34])=[N:28][N:27]([CH3:26])[CH:31]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 5-chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.076 g, 0.20 mmol) and EtOH (4.0 mL) was added 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (0.027 g, 0.22 mmol) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.85 mL, 0.85 mmol). The reaction mixture was stirred at 80° C. for 24 h, it was then allowed to cool to room temperature, concentrated in vacuo, and the residue was absorbed on silica gel and placed on a 10 g isolute silica column. Elution with ethyl acetate/dichloromethane (v/v; 1:1), and then 4% methanol in ethyl acetate/dichloromethane (v/v; 1:1) afforded the title compound as a white solid after trituration with diethyl ether (0.023 g, 25%).

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
customthe residue was absorbed on silica gel
washElution with ethyl acetate/dichloromethane (v/v; 1:1)

Sources & evidence

ORD record: ord-e9fbdd2da7994bfc8862a96b29e04a89
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447092B2

Reaction notes

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