3-Fluorophenyl isocyanate → HCID 45140728, compound

HRID 552400Notes

Reaction equation

HRID 552400 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:21]=[C:22]([N:26]=[C:27]=[O:28])[CH:23]=[CH:24][CH:25]=1>>[F:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH:1][C:2]2[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]3[CH:11]=[CH:10][N:9]=[C:8]4[NH:12][C:13](=[O:15])[NH:14][C:7]=34)[CH:3]=2)=[O:28])[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45140728HCID 45140728, compoundYield 16%

Procedure

Method G was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-fluoro-phenylisocyanate to afford the title compound (10 mg, 16%). 1H-NMR (DMSO), δ (ppm), J (Hz): 6.40 (d, 1H, HPyr, J=5.9 Hz), 6.74-6.79 (m, 1H, Harom2′), 7.21 (d, 1H, Harom4 or 6, J=8.05 Hz), 7.27 (d, 1H, Harom6 or 4), 7.30-7.46 (m, 5H, Harom4′, Harom5′, Harom6′, Harom2, Harom 5), 7.79 (d, 1H, HPyr), 9.04 (s, 2H, NHurea), 11.17 (s, 1H, NHim), 11.37 (s, 1H, NHim); MS-LC, Rf=6.84 min, (C19H14FN5O3), m/z: 380.1 [M++H], 100.

Sources & evidence

ORD record
ord-843c922a1a334ff3921b2791d5bea2e4
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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