3-(1,1,2,2-Tetrafluoroethoxy)benzoic acid → HCID 45141565, compound

HRID 552435Notes

Reaction equation

HRID 552435 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]([F:34])([O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29])[CH:21]([F:23])[F:22]>>[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:28](=[O:29])[C:27]4[CH:31]=[CH:32][CH:33]=[C:25]([O:24][C:20]([F:19])([F:34])[CH:21]([F:22])[F:23])[CH:26]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 5786803-(1,1,2,2-Tetrafluoroethoxy)benzoic acidHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141565HCID 45141565, compoundYield 36%

Procedure

Method H2 was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-(1,1,2,2-tetrafluoroethoxy)benzoic acid to afford the title compound as a light pink solid (69 mg, 36%). 1H-NMR (δ, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=5.8 Hz), 6.86 (t, 1H, CF2H, J=51.7 Hz), 6.94 (d, 1H, Harom, J=7.2 Hz), 7.44 (t, 1H, Harom, J=8.2 Hz), 7.54 (d, 1H, Harom, J=7.6 Hz), 7.62-7.67 (m, 3H, Harom), 7.80-7.82 (m, 2H, Harom), 7.95 (d, 1H, Harom, J=7.8 Hz) 10.49 (s, 1H, NHamide), 11.25 (s, 1H, NHurea), 11.44 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 105.81 (CF2), 106.61, 107.79 (CF2) 110.90, 113.78, 114.68, 116.38, 120.76, 124.77, 126.26, 130.2, 130.40, 136.62, 140.51, 141.35, 144.60, 147.17, 148.04, 154.22, 154.75, 164.17. HRMS (EI): m/z [M+H] calcd for C21H14F4N4O4: 463.1024, found: 463.1022.

Sources & evidence

ORD record
ord-a22e0a1687b94f7e8544df13f7e582d3
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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