Ammonia → 1-(4-Fluorophenyl)-6-(2-(2-methylpyrimidin-5-yl)ethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1048888Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]4[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=4)=[CH:15][CH:16]=3)[C:11](=[O:27])[C:10]([C:28](OCC)=[O:29])=[CH:9]2)=[CH:4][CH:3]=1.[NH3:33]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]4[CH:25]=[N:24][C:23]([CH3:26])=[N:22][CH:21]=4)=[CH:15][CH:16]=3)[C:11](=[O:27])[C:10]([C:28]([NH2:33])=[O:29])=[CH:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Compound T (11 mg, 0.026 mmol, 1.0 eq) was dissolved in 7N ammonia in methanol (1 mL) in a microwave vial and heated in a microwave reactor at 150° C. for 60 minutes. The reaction was concentrated and purified by reverse phase chromatography to afford 6.7 mg (65%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.24 (d, J=4.4 Hz, 1H), 8.55 (s, 2H), 8.53 (s, 1H), 8.20 (d, J=2.0 Hz, 1H), 7.76-7.71 (m, 2H), 7.62-7.58 (m, 2H), 7.51 (t, J=8.7 Hz, 2H), 6.99 (d, J=8.7 Hz, 1H), 3.06 (t, J=8.3 Hz, 2H), 2.90 (t, J=8.3 Hz, 2H), 2.53 (s, 3H); ES-MS [M+1]+: 403.2.

Workup

concentrationThe reaction was concentrated
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-73e571d21ff448bd99861d3738d4fff3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382208B1

Reaction notes

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