3-(Trifluoromethoxy)benzoyl chloride → HCID 45140730, compound

HRID 552437Notes

Reaction equation

HRID 552437 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([F:20])[C:5]([F: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:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>>[NH2:14][C:10]1[C:9]([N+:15]([O-:17])=[O:16])=[C:8]([O:7][C:6]2[C:5]([F:19])=[C:4]([F:20])[C:3]([F:21])=[C:2]([NH:1][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([O:24][C:23]([F:22])([F:34])[F:35])[CH:26]=3)[CH:18]=2)[CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 45140344HCID 45140344, compound

Product 1

HCID 45140730HCID 45140730, compoundYield 57%

Procedure

Method H was used with 4-(5-amino-2,3,4-trifluorophenoxy)-3-nitropyridin-2-amine and 3-(trifluoromethoxy)benzoyl chloride to afford the title compound (140 mg, 57%). 1H NMR δ (DMSO): 6.26 (d, 1H, Hpy,5, J=5.5 Hz), 7.35 (s, 2H, NH2), 7.55 (t, 1H, Harom,6′, J=6.5 Hz), 7.66 (d, 1H, Harom), 7.71 (t, 1H, Harom,5″, J=8.0 Hz), 7.91 (s, 1H, Harom,2″), 8.00 (d, 1H, Harom), 8.08 (d, 1H, HPy,6, J=5.5 Hz), 10.63 (s, 1H, NHamide). 19F NMR δ (DMSO): −56.28 (s, 3F, CF3), −141.42 (d, 1F, aromF, J=21.5 Hz), −152.31 (d, 1F, aromF, J=21.5 Hz), −156.04 (t, 1F, F3, J=21.5 Hz).

Sources & evidence

ORD record
ord-f572a2a880324054aee8e83bae6c7639
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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