N-Ethyl-3-nitropyridin-4-amine → HCID 73855033, compound

HRID 1241971Notes

Reaction equation

HRID 1241971 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-])=O)[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:24]([N:31]1[C:35](=[O:36])[C:34](=[C:37]2[N:41]([CH3:42])[C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[S:38]2)[S:33][CH2+:32]1SC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([N:31]1[C:35](=[O:36])[C:34](=[C:37]2[N:41]([CH3:42])[C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[S:38]2)[S:33][C:32]1=[N:10][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[NH:3][CH2:1][CH3:2])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

2

Reactant 1

HCID 21937597N-Ethyl-3-nitropyridin-4-amine

Product 1

HCID 73855033HCID 73855033, compound

Procedure

In a manner similar to Example 30, intermediate 4-ethylamino-3-nitropyridine was hydrogenated and then condensed with 3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate to afford the title compound. 1H-NMR (CDCl3): δ 8.04–8.09 (2H, m), 7.53 (1H, d), 7.44–7.48 (2H, m), 7.27–7.38 (4H, m), 7.19 (1H, m), 7.07 (1H, d), 6.42 (1H, d), 5.19 (2H, s), 4.12 (1H, br t), 3.79 (3H, s), 3.02 (2H, m), 1.05 (3H, t); MS(ESI): 474 (MH+).

Sources & evidence

ORD record
ord-5a4fb21dcf264e12965121dfae389741
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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