2-Fluoro-5-(trifluoromethoxy)benzoyl chloride → HCID 45141563, compound

HRID 552431Notes

Reaction equation

HRID 552431 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[F:19][C:20]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][C:21]=1[C:22](Cl)=[O:23]>>[O:15]=[C:13]1[NH:12][C:8]2=[N:9][CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:22](=[O:23])[C:21]4[CH:25]=[C:26]([O:29][C:30]([F:31])([F:32])[F:33])[CH:27]=[CH:28][C:20]=4[F:19])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 51025512-Fluoro-5-(trifluoromethoxy)benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141563HCID 45141563, compoundYield 11.7%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 2-fluoro-5-trifluoromethoxy-benzoyl chloride to afford the title compound (11 mg, 11.7%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=5.9 Hz), 6.91-6.94 (m, 1H, Harom), 7.41-7.44 (m, 2H, Harom), 7.50-7.53 (m, 2H, Harom), 7.67-7.69 (m, 1H, Harom), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 10.65 (s, 1H, NHamide), 11.18 (s, 1H, NHPy7), 11.39 (s, 1H, NHPy9). LC-MS, tR=4.65 minutes, m/z: 449.08 (M+H)+, calculated for C20H13N4O4F4. HRMS (EI): m/z [M+H] calculated for C20H13N4O4F4: 449.0873; found: 449.0873.

Sources & evidence

ORD record
ord-b644bfa75d2140599e26b43334362dbf
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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