Hydrochloric Acid → 4-(5-chloro-4-(3-methylpiperidin-4-yloxy)-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrile hydrochloride

HRID 386589Notes

Reaction equation

HRID 386589 reaction equation
[Cl:1][C:2]1[C:3]([O:18][C@@H:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][C@H:20]2[CH3:32])=[CH:4][C:5](=[O:17])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=2)[CH:7]=1.Cl>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[CH3:32])=[CH:4][C:5](=[O:17])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131730204trans-Tert-butyl 4-(5-chloro-1-(4-cyano-3-fluorophenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)-3-methylpiperidine-1-carboxylate

Product 1

HCID 670726194-(5-chloro-4-(3-methylpiperidin-4-yloxy)-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrile hydrochlorideYield 229.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-tert-butyl 4-(5-chloro-1-(4-cyano-3-fluorophenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)-3-methylpiperidine-1-carboxylate (200 mg, 0.433 mmol) in MeOH (1.0 mL) at room temperature was added hydrochloric acid (2.5 mL, 10.00 mmol, 4.0 M in dioxane). The reaction mixture was stirred for 30 min and then evaporated under reduced pressure. The residue was co-evaporated with ethanol (2×) to give 198 mg of the title compound as an orange solid. This material was used in the next step without further purification. MS (ESI) 362 (M+H).

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f4704d91bcc14e40a20c035e60b79e81
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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