4-Nitrophenethylamine → HCID 58808659, compound

HRID 1921500Notes

Reaction equation

[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:17]([OH:19])=O)[CH:16]=2)[CH:4]=1)[CH3:2].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=1)([O-:22])=[O:21]>>[N+:20]([C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][NH:31][C:17]([C:15]2[CH:16]=[C:11]([C:5]3[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=3[CH3:10])[CH:12]=[N:13][CH:14]=2)=[O:19])=[CH:27][CH:28]=1)([O-:22])=[O:21]

Participants

Reactant 2

HCID 951534-Nitrophenethylamine

HCID 588087025'-Ethyl-2'-methyl-6'-oxo-1',6'-dihydro-[3,3']bipyridinyl-5-carboxylic acid

Product 1

HCID 58808659HCID 58808659, compound

Procedure

Method 1, Example 205 is substantially repeated except for utilizing 5′-ethyl-2′-methyl-6′-oxo-1′,6′-dihydro-[3,3′]bipyridinyl-5-carboxylic acid and 2-(4-nitro-phenyl)-ethyl-amine to afford the title compound. MS: m/e=407 (M+H). 1H NMR (δ ppm): 11.72 (s, 1H); 8.87 (d, 1H, J=2.1 Hz); 8.78 (t, 1H, J=5.4 Hz); 8.68 (d, 1H, 2.1 Hz); 8.17 (d, 2H, J=8.6 Hz); 8.05 (t, 1H, J=2.1 Hz); 7.55 (d, 2H, J=8.6 Hz); 7.27 (s, 1H); 3.58 (m, 2H); 3.02 (t, 2H, J=7.1 Hz); 2.43 (q, 2H, J=7.4 Hz); 2.17 (s, 3H); 1.11 (t, 3H, J=7.4 Hz).

Sources & evidence

ORD record: ord-bb05cca58a874cfabc15ffd3703a7513
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173682B2

Reaction notes

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