3-(Trifluoromethoxy)benzoyl chloride → HCID 45140537, compound

HRID 552439Notes

Reaction equation

HRID 552439 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[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:3]=[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:18]=[C:17]([Cl:19])[CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 45140147HCID 45140147, compound

Product 1

HCID 45140537HCID 45140537, compoundYield 74%

Procedure

Method H was used with 4-(3-Amino-5-chlorophenoxy)-3-nitropyridin-2-amine and 3-(trifluoromethoxy)benzoyl chloride to afford the title compound as a yellow solid (0.155 g, 74%). 1H NMR δ (DMSO): 6.21 (d, 1H, Hpy,5, J=5.5 Hz), 7.13 (t, 1H, Harom, J=2 Hz), 7.25 (s, 2H, NH2), 7.58 (t, 1H, Harom, J=2 Hz), 7.63 (dt, 1H, Harom, J=1+8 Hz), 7.70 (t, 1H, Harom,5, J=8 Hz), 7.86 (d, 1H, Harom, J=2 Hz), 7.89 (s, 1H, Harom,2′), 8.02 (dt, 1H, Harom, J=1+8 Hz), 8.09 (d, 1H, Hpy,6, J=5.5 Hz), 10.6 (s, 1H, NHamide). 19F NMR 6 (DMSO): −56.77 (s, 3F, CF3). MS m/z 469/71(M++1).

Sources & evidence

ORD record
ord-23215cbfa14d4762b926e62f33942d09
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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