3-(Trifluoromethoxy)benzoyl chloride → HCID 45140536, compound

HRID 552438Notes

Reaction equation

HRID 552438 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[C:7]=1[N+:13]([O-:15])=[O:14].[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>>[NH2:12][C:8]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]([O:5][C:4]2[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([O:22][C:21]([F:20])([F:32])[F:33])[CH:24]=3)[CH:3]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 45140146HCID 45140146, compound

Product 1

HCID 45140536HCID 45140536, compoundYield 33%

Procedure

Method H was used with 4-(3-amino-4-chlorophenoxy)-3-nitropyridin-2-amine and 3-(trifluoromethoxy)benzoyl chloride to afford the title compound as a yellow solid (0.153 g, 33%). 1H NMR δ (DMSO): 6.11 (d, 1H, Hpy,5, J=5.5 Hz), 7.18 (dd, 1H, Harom,5, J=3+9 Hz), 7.23 (s, 2H, NH2), 7.53 (d, 1H, Harom,2, J=3 Hz), 7.63 (dt, 1H, Harom, J=1+8 Hz), 7.66 (d, 1H, Harom,6, J=9 Hz), 7.70 (t, 1H, Harom,5, J=8 Hz), 7.91 (s, 1H, Harom,2′), 8.02 (dt, 1H, Harom, J=1+8 Hz), 8.07 (d, 1H, Hpy,6, J=5.5 Hz), 10.63 (s, 1H, NHamide). 19F NMR δ (DMSO): −56.37 (s, 3F, CF3).

Sources & evidence

ORD record
ord-28148f5bfb364d41b1e0fbf1a3150599
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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