2-(Thiomorpholin-4-yl)pyridine-4-carboxylic acid → HCID 45142202, compound

HRID 552433Notes

Reaction equation

HRID 552433 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.[S:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][N:33]=2)[C:28](O)=[O:29])[CH2:21][CH2:20]1>>[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][N:33]=[C:25]([N:22]5[CH2:21][CH2:20][S:19][CH2:24][CH2:23]5)[CH:26]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 185258482-(Thiomorpholin-4-yl)pyridine-4-carboxylic acidHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142202HCID 45142202, compoundYield 50%

Procedure

Method Method H2 was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 2-thiomorpholinoisonicotinic acid to afford the title compound as a light pink solid (93 mg, 50%). 1H-NMR (δ, ppm, DMSO-d6): 2.62 (d, 4H, HThiomorph, J=7.2 Hz), 3.96 (d, 4H, HThiomorph, J=7.2 Hz), 6.49 (d, 1H, HPy,5, J=5.9 Hz), 6.93 (dd, 1H, Harom, J=7.9 Hz, J=1.8 Hz), 7.01 (d, 1H, Harom, J=5.1 Hz), 7.19 (s, 1H, Harom), 7.43 (t, 1H, Harom, J=8.2 Hz), 7.60-7.64 (m, 2H, Harom), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 8.25 (d, 1H, Harom, J=5.1 Hz), 10.39 (s, 1H, NHamide), 11.19 (s, 1H, NHurea), 11.39 (s, 1H, NHurea). 13C-NMR (δ, ppm, DMSO-d6): 25.18 (CThiomorph), 47.14 (CThiomorph), 105.01, 106.50, 110.05, 110.75, 113.67, 114.63, 116.26, 130.08, 140.24, 141.28, 143.63, 144.42, 147.04, 148.30, 154.08, 154.64, 158.13, 164.81. HRMS (EI): m/z [M+H] calculated for C22H20N6O3S: 449.1390, found: 449.1396.

Sources & evidence

ORD record
ord-110dfc1e36d040dd923347e0f01b29b8
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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