Sodium hydride → HCID 49853593, compound

HRID 476188Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([C:35]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:36])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:25])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 100 mg, 0.25 mmol) in dry DMF (5 mL), sodium hydride (12 mg, 0.27 mmol) was added at 0° C. under nitrogen atmosphere. After 15 minutes morpholine-4-carbonyl chloride (56.1 mg, 0.37 mmol) was added, and the reaction mixture was heated at 60° C. for 48 hours. The reaction mixture was concentrated in vacuum. The crude product was purified by column chromatography (silica gel, 3% acetone in chloroform) to obtain the title compound. Yield: 15 mg (11.73%); 1H NMR (CDCl3, 300 MHz): δ 9.09 (s, 1H), 7.973-8.004 (d, 1H, J=9.3 Hz), 7.772-7.8 (d, 2H, J=8.4 Hz), 7.621-7.658 (dd, 1H, J=9 Hz, 2.1 Hz), 7.517-7.545 (d, 2H, J=8.4 Hz,), 7.057-7.064 (d, 1H, J=2.1 Hz), 3.67 (t, 4H,), 3.26 (t, 4H), 1.84 (s, 6H); MS: m/z 520 (M+).

Workup

concentrationThe reaction mixture was concentrated in vacuum
customThe crude product was purified by column chromatography (silica gel, 3% acetone in chloroform)

Sources & evidence

ORD record: ord-f400f2b3425049d098f50c2504e2c1c3
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637670B2

Reaction notes

Loading…