4-(Dimethylamino)Benzaldehyde → HCID 178482687, compound

HRID 416711Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:5]([Br:24])=[CH:4][N:3]=1.[CH3:25][N:26]([CH3:35])[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:6]2[C:5]([Br:24])=[CH:4][N:3]=[C:2]3[NH:1][C:31]([C:30]4[CH:33]=[CH:34][C:27]([N:26]([CH3:35])[CH3:25])=[CH:28][CH:29]=4)=[N:8][C:7]=23)[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To tert-butyl 4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazine-1-carboxylate (0.5 g, 1.2 mmol) in EtOH (20 mL) was added 4-dimethylaminobenzaldehyde (0.241 g, 1.6 mmol), and 1M Na2S2O4 (4.7 mL, 4.7 mmol) The reaction mixture was stirred at 80° C. for 16 h then concentrated in vacuo. The residue was purified by chromatography (100% dichloromethane to dichloromethane/ethyl acetate 1/1, 2% MeOH in dichloromethane/ethyl acetate 1/1, and 2% MeOH in CHCl3). The compound is further triturated in dichloromethane/methanol 9/1, filtered and dried in vacuo to give the title compound as a solid (0.394 g, 63% yield).

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by chromatography (100% dichloromethane to dichloromethane/ethyl acetate 1/1, 2% MeOH in dichloromethane/ethyl acetate 1/1, and 2% MeOH in CHCl3)
customThe compound is further triturated in dichloromethane/methanol 9/1
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-5bc79b26eef34995991a21f439bd67b6
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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