Acetaldehyde → tert-butyl(1-(4-(3-hydroxy-2-methyl-8-phenyl-4,5-dihydro-3H-imidazo[4,5-f]quinolin-7-yl)phenyl)cyclobutyl)carbamate

HRID 1509091Notes

Reaction equation

[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=O)[C:23](=[N:35][OH:36])[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:38](=O)[CH3:39].[OH-].[NH4+:42]>C(O)C>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24]5[N:42]=[C:38]([CH3:39])[N:35]([OH:36])[C:23]=5[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl(1-(4-(6-(hydroxyimino)-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (300 mg, 0.603 mmol) in ethanol (3.0 mL) was added acetaldehyde (68.1 μl, 1.206 mmol) followed by ammonium hydroxide (329 μl, 2.53 mmol). The reaction mixture was heated at 80° C. under a nitrogen atmosphere for 2 hours, then allowed to cool to room temperature and concentrated to dryness under reduced pressure and dried to give the crude product as a brown solid (306 mg, 97% yield).

Workup

temperatureto cool to room temperature
concentrationconcentrated to dryness under reduced pressure
customdried

Sources & evidence

ORD record: ord-1284da05401042d3b1e8b0af9629fcf8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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