Cyclopentanone → N-Methyl 2-fluoro-4-(1-cyanocyclopentyl)aminobenzamide

HRID 245031Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[F:11].[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.[Si]([C:23]#[N:24])(C)(C)C>C(OCC)(=O)C>[CH3:1][NH:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:13]2([C:23]#[N:24])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][C:5]=1[F:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-Methyl-2-fluoro-4-aminobenzamide (Formula 39) (62 mg, 0.37 mmol), cyclopentanone (0.07 mL, 0.74 mmol) and TMSCN (0.1 mL, 0.74 mmol) was heated to 80° C. and stirred for 13 h. To the medium was added ethyl acetate (2×20 mL) and then washed with water (2×20 mL). The organic layer was dried over MgSO4 and concentrated and the residue was purified with silica gel column chromatography (dichloromethane:acetone, 95:5) to give N-Methyl 2-fluoro-4-(1-cyanocyclopentyl)aminobenzamide (Formula 43) (61 mg, 63%) as a white solid. 1H NMR δ 7.95 (dd, 1H, J=8.8, 8.8 Hz), 6.65 (br s, 1H), 6.59 (dd, 1H, J=8.8, 2.3 Hz), 6.50 (dd, 1H, J=14.6, 2.3 Hz), 4.60 (br s, 1H), 2.99 (dd, 3H, J=4.8, 1.1 Hz), 2.36-2.45 (m, 2H), 2.10-2.18 (m, 2H), 1.82-1.95 (m, 4H).

Workup

washwashed with water (2×20 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 95:5)

Sources & evidence

ORD record: ord-c67c1997fc5c43bfb19db231f7996dca
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658681B2

Reaction notes

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