Hydrochloric Acid → 5-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one Hydrochloric Acid Salt

HRID 1962283Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:20][CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)=[CH:4][C:5](=[O:19])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:10]([F:18])[CH:9]=2)[CH:7]=1.Cl>>[ClH:1].[Cl:1][C:2]1[C:3]([O:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:4][C:5](=[O:19])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:10]([F:18])[CH:9]=2)[CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 58467945Tert-butyl 4-(5-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 674373435-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one Hydrochloric Acid SaltYield 199.3%

Procedure

A mixture of tert-butyl 4-(5-chloro-1-(3-fluoro-4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (300 mg, 0.599 mmol) and hydrogen chloride (37% in H2O, 5 mL) was stirred for 15 min and then concentrated in vacuo to yield 261 mg of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (br s, 2H) 8.11 (s, 1H) 7.97 (t, J=8.16 Hz, 1H) 7.78 (dd, J=10.92, 1.88 Hz, 1H) 7.57 (dd, J=8.28, 1.76 Hz, 1H) 6.30 (s, 1H) 4.80-491 (m, 1H) 3.39 (s, 3H) 3.05-3.26 (m, 4H) 2.10-2.20 (m, 2H) 1.85-1.98 (m, 2H). MS (ESI) 401 (M+H).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d3489c187c164c0c8bd396d3098862db
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415367B2

Reaction notes

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