Ethanol → (S)-(6-(4-amino-1H-pyrazol-1-yl)-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)(cyclopropyl)methanone

HRID 1051714Notes

Reaction equation

[CH:1]1([C:4]([N:6]2[C:15]3[C:10](=[C:11]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:12]([N:16]4[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]4)=[CH:13][CH:14]=3)[CH2:9][CH2:8][C@@H:7]2[CH3:31])=[O:5])[CH2:3][CH2:2]1.[Cl-].[NH4+].O1CCCC1.C(O)C>[Fe].O>[NH2:21][C:19]1[CH:18]=[N:17][N:16]([C:12]2[C:11]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:10]3[C:15](=[CH:14][CH:13]=2)[N:6]([C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[C@@H:7]([CH3:31])[CH2:8][CH2:9]3)[CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (S)-cyclopropyl(2-methyl-6-(4-nitro-1H-pyrazol-1-yl)-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)methanone (0.060 g, 0.15 mmol), iron powder (0.040 g, 0.72 mmol), ammonium chloride (0.023 g, 0.43 mmol), tetrahydrofuran (4 mL), ethanol (4 mL), and water (1 mL) stirred overnight at 80° C. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum, and the residue was purified by preparative thin layer chromatography (eluting with 1:1, ethyl acetate/petroleum ether) to afford (S)-(6-(4-amino-1H-pyrazol-1-yl)-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)(cyclopropyl)methanone (0.045 g, 81%) as a brown solid. MS (ESI, pos. ion) m/z 389 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated under vacuum
customthe residue was purified by preparative thin layer chromatography (eluting with 1:1, ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-41052a8365ca49789496255f96bc8984
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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