Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-thiazol-4-ylmethyl-1H-quinolin-4-one

HRID 226935Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Cl.Cl[CH2:26][C:27]1[N:28]=[CH:29][S:30][CH:31]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:26][C:27]2[N:28]=[CH:29][S:30][CH:31]=2)[CH:8]=1)=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound 4j was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 50 mg (0.18 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one 3a, 19 mg (0.47 mmol) of 60% sodium hydride and 40 mg (0.25 mmol) of 4-chloromethyl thiazole hydrochloride were combined in 1 mL N,N-dimethylformamide and stirred at 70° C. for 2 h. The crude product was purified by flash chromatography using 20-100% ethyl acetate in hexane yielded 54 mg of the product as white solid: LC-MSD, m/z for C22H18N2O2S [M+H]+=375.5; HPLC retention time: 2.1 min; 1H NMR (400 MHz, CDCl3): δ 2.3 (s, 3H), 2.35 (s, 3H), 5.6 (s, 2H), 7.1-7.2 (m, 2H), 7.4-7.5 (m, 1H), 7.5-7.6 (m, 2H), 7.6-7.7 (m, 2H), 8.3 (s, 1H), 8.45-8.5 (m, 1H), 8.8-8.85 (m, 1H).

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-f6b405aad8bb45908bf24ab6aba5efb4
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557213B2

Reaction notes

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