HCID 69217114, compound → HCID 136018652, compound

HRID 2053435Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:14][CH2:15][CH:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[N:17]=1)=[C:5]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:14][CH:15]=[C:16]([CH2:18][CH:19]([CH3:21])[CH3:20])[N:17]=1)=[C:5]2[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 6-chloro-3-(4-isobutyl-4,5-dihydro-oxazol-2-yl)-4-phenyl-1H-quinolin-2-one (c) (10.0 mg, 0.025 mmol), MnO2 (15 mg) and CHCI3 (1.0 mL) in a sealed tube was heated at 125° C. for 45 min in a microwave reactor (Smith Synthesizer). The mixture was then filtered through a small pad of celite and purified by prep TLC (5% MeOH/EtOAc) to afford 6-chloro-3-(4-isobutyl-oxazol-2-yl)-4-phenyl-1H-quinolin-2-one (d) (2 mg, 20%). 1H NMR (acetone-d6): δ 11.20 (b s, 1 H), 7.60-7.20 (m, 9 H), 2.20 (d, 2 H), 1.80-1.65 (m, 1 H), 0.75 (d, 6 H). LCMS: 379.3 (M+H).

Workup

filtrationThe mixture was then filtered through a small pad of celite
custompurified by prep TLC (5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-935a2433e23b43f8928646698c8a2f9e
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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