Resorcinol → HCID 89783750, compound

HRID 1055933Notes

Reaction equation

HRID 1055933 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Cl[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:20]3[NH:28][C:27]4[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=4[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[N:11]=1>>[OH:2][C:1]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[O:5][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:20]3[NH:28][C:27]4[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=4[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

3

Reactant 2

HCID 5054ResorcinolHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783750HCID 89783750, compoundYield 78%

Conditions

Temperature
90 °C

Procedure

Prepared according to Example 103 using resorcinol (125.5 mg, 1.140 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50.0 mg, 0.168 mmol), heating at 90° C. for 18 h. Chromatographic purification (silica gel, 0-10% MeOH/DCM) furnished 2-(2-(3-hydroxyphenoxy)-quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (48.4 mg, 0.130 mmol, 78% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.20 (1H, br. s.), 9.86 (1H, s), 8.47 (1H, d, J=8.8 Hz), 8.14 (1H, d, J=7.6 Hz), 7.78 (1H, d, J=7.2 Hz), 7.47 (1H, t, J=7.7 Hz), 7.35-7.42 (2H, m), 6.98 (1H, d, J=2.2 Hz), 6.94 (1H, br. s.), 6.83 (1H, m, J=7.8, 1.8 Hz), 6.79 (1H, dd, J=7.9, 1.7 Hz), 6.74 (1H, t, J=2.2 Hz), 3.31-3.37 (2H, m), 2.47-2.49 (2H, obsc. m). m/z (ESI, +ve) 372.0 (M+H)+.

Workup

  1. customPrepared
  2. customChromatographic purification (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-55b3e59ff70c4a708e6a06a723f0ce66
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…