1-benzothiophene-5-carbonyl chloride → HCID 45141967, compound

HRID 552419Notes

Reaction equation

HRID 552419 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[CH:23]=[CH:22][C:21]2[CH:24]=[C:25]([C:28](Cl)=[O:29])[CH:26]=[CH:27][C:20]1=2>>[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]([C:25]4[CH:26]=[CH:27][C:20]5[S:19][CH:23]=[CH:22][C:21]=5[CH:24]=4)=[O:29])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 27954451-benzothiophene-5-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141967HCID 45141967, compoundYield 30%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and benzo[b]thiophene-5-carbonyl chloride to afford the title compound (25 mg, 30%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.91 (d, 1H, Harom, J=7.0 Hz), 7.43 (t, 1H, Harom, J=8.0 Hz), 7.60 (d, 1H, Harom, J=5.0 Hz), 7.67 (t, 1H, Harom, J=2.5 Hz), 7.81 (d, 1H, HPy,6, J=6.0 Hz), 7.89 (d, 1H, Harom, J=6.0 Hz), 7.91 (d, 1H, Harom, J=8.0 Hz), 8.15 (d, 1H, Harom, J=8.5 Hz), 8.49 (d, 1H, Harom, J=1.5 Hz), 10.44 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C21H15N4O3: 403.0865; found: 403.0867.

Sources & evidence

ORD record
ord-31dfd70a9844481a9b1740880e115c51
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

Loading…