Hydrochloric Acid → 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(4,5-dimethyl-6-(2-oxo-1,2-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

HRID 870019Notes

Reaction equation

[F:1][C:2]1([F:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[C:24]([O:29]C)=[N:25][CH:26]=[CH:27][CH:28]=5)[C:20]([CH3:31])=[C:19]([CH3:32])[CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.Cl.C(N(CC)CC)C>O1CCOCC1>[F:33][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[C:19]([CH3:32])[C:20]([CH3:31])=[C:21]([C:23]5[C:24](=[O:29])[NH:25][CH:26]=[CH:27][CH:28]=5)[N:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-methoxy-3,4-dimethyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (40 mg, 0.09 mmol) in dioxane (1 mL) was added 4M HCl and the reaction was stirred at 90° C. for 3 hours. To the mixture at room temperature, 0.5 mL of triethyl amine was added and the reaction was concentrated under reduced pressure. The crude residue was purified by column chromatography using a gradient of ethyl acetate in hexanes (50-100%). ESI-MS m/z calc. 439.4. found 440.3 (M+1)+. Retention times: 1.39 minutes. H NMR (400 MHz, DMSO) 8.67 (s, 1H), 7.80 (s, 1H), 7.55 (d, J=1.5 Hz, 1H), 7.44-7.32 (m, 4H), 6.23 (t, J=6.6 Hz, 1H), 2.27 (s, 3H), 1.96 (s, 3H), 1.51-1.48 (m, 2H), 1.16-1.14 (m, 2H).

Workup

concentrationthe reaction was concentrated under reduced pressure
customThe crude residue was purified by column chromatography
custom1.39 minutes

Sources & evidence

ORD record: ord-8d8a8b31754a42f794f1f359a7946629
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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