3-(Trifluoromethyl)phenyl isocyanate → HCID 58024438, compound

HRID 552404Notes

Reaction equation

HRID 552404 reaction equation
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[C:9]=1[N+:15]([O-:17])=[O:16].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>>[NH2:14][C:10]1[C:9]([N+:15]([O-:17])=[O:16])=[C:8]([O:7][C:6]2[C:5]([Cl:19])=[CH:4][C:3]([Cl:20])=[C:2]([NH:1][C:30]([NH:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=3)=[O:31])[CH:18]=2)[CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 45140340HCID 45140340, compound

Product 1

HCID 58024438HCID 58024438, compoundYield 58%

Procedure

Method G was used with 4-(5-amino-2,4-dichlorophenoxy)-2-amino-3-nitropyridine and 3-trifluoromethylphenyl isocyanate to afford the title compound as a yellow solid (92 mg, 58%). 1H-NMR (δ, ppm, DMSO-d6): 6.01 (d, 1H, HPy,5, J=5.6 Hz), 7.26 (s, 2H, NH2,Py), 7.35-7.37 (m, 1H, Harom), 7.53-7.55 (m, 2H, Harom), 7.90 (s, 1H, Harom), 7.98 (s, 1H, Harom), 8.03 (d, 1H, HPy,6, J=5.6 Hz), 8.24 (s, 1H, Harom), 8.62 (s, 1H, NHurea), 9.86 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 99.6 (C-4); 113.9 (C-11); 114.1 (C-14); 118.4 (C-2); 118.7 (C-16); 119.4 (C-7); 121.0 (C-18); 121.9 (C-9); 125.1 (C-15); 129.5 (C-19); 130.0 (C-17); 130.4 (C-8); 136.3 (C-10); 139.7 (C-13); 147.3 (C-6); 151.7 (C-12); 153.4 (C-5); 153.8 (C-1); 157.6 (C-3). LC-MS (m/z): 501 (M+H, 100).

Sources & evidence

ORD record
ord-1eee22bd5921455dbde9359d7b70f1c6
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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