2-Chloropyridine-4-carbonyl chloride → HCID 45142198, compound

HRID 552422Notes

Reaction equation

HRID 552422 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.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][N:28]=1)[C:23](Cl)=[O:24]>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][N:28]=1)[C:23]([NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:12][C:13](=[O:15])[NH:14][C:7]=23)[CH:3]=1)=[O:24]

Participants

3

Reactant 2

HCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142198HCID 45142198, compoundYield 49%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 2-chloroisonicotinoyl chloride to afford the title compound (39 mg, 49%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.96 (d, 1H, Harom, J=8.0 Hz), 7.45 (t, 1H, Harom, J=8.0 Hz), 7.59 (t, 1H, Harom, J=2.0 Hz), 7.64 (d, 1H, Harom, J=8.0 Hz), 7.82 (d, 1H, HPy,6, J=6.0 Hz), 7.85 (d, 1H, Harom, J=5.0 Hz), 7.97 (s, 1H, Harom), 7.61 (d, 1H, Harom, J=5.0 Hz), 10.66 (s, 1H, NHamide), 11.21 (s, 1H, NHPy3), 11.42 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C18H13N5O3Cl: 382.0707; found: 382.0702.

Sources & evidence

ORD record
ord-dd78d693d0084056b992ff768bee3aa5
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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