Benzoyl chloride → HCID 49853689, compound

HRID 476191Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[NH:14][C:15](=[O:28])[N:16]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:19][CH:18]=4)[C:7]=3[C:6]=2[CH:5]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[C:29]([N:14]1[C:8]2[CH:9]=[N:10][C:11]3[CH:12]=[CH:13][C:4]([Br:3])=[CH:5][C:6]=3[C:7]=2[N:16]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:27])[C:24]#[N:25])=[CH:19][CH:18]=2)[C:15]1=[O:28])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (30 mg, 0.75 mmol) was added to dry DMF (5 ml) in a nitrogen atmosphere. The reaction flask was cooled in an ice-bath to 0° C., and 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) was added. After 15 minutes benzoyl chloride (42 mg, 0.29 mmol) was added, and the reaction mixture was heated at 50° C. for 24 hours. The reaction mixture was concentrated in vacuum. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 13 mg (10%); 1H NMR (DMSO-d6, 300 MHz): δ 9.410 (s, 1H), 7.998-8.028 (d, 1H, J=9 Hz), 7.939-7.963 (d, 2H, J=7.2 Hz), 7.848-7.876 (d, 2H, J=8.4 Hz), 7.764-7.792 (d, 3H, J=8.4 Hz), 7.644-7.669 (m, 1H), 7.48-7.56 (m, 2H), 6.865-6.872 (d, 1H, J=2.1 Hz), 1.78 (s, 6H); MS: m/z 511 (M+1).

Workup

temperaturethe reaction mixture was heated at 50° C. for 24 hours
concentrationThe reaction mixture was concentrated in vacuum
customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

Sources & evidence

ORD record: ord-544c3647a8f14c7e9d1504b7269870b1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637670B2

Reaction notes

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