Tert-butyl 4-[(3,6-dichloro-2-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}pyridin-4-yl)(methyl)amino]piperidine-1-carboxylate → 3,6-dichloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-4-[methyl(piperidin-4-yl)amino]pyridine-2-carboxamide hydrochloride

HRID 2208799Notes

Reaction equation

HRID 2208799 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:16]2[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([C:23](=[O:35])[NH:24][CH2:25][C:26]3[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])[C:17]=2[Cl:36])[CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:22].[Cl:36][C:17]1[C:18]([C:23]([NH:24][CH2:25][C:26]2[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=2[CH3:32])=[O:35])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[N:14]([CH3:15])[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 86719555Tert-butyl 4-[(3,6-dichloro-2-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}pyridin-4-yl)(methyl)amino]piperidine-1-carboxylate

Product 1

HCID 867195563,6-dichloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-4-[methyl(piperidin-4-yl)amino]pyridine-2-carboxamide hydrochlorideYield 14%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl4-[(3,6-dichloro-2-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}pyridin-4-yl)(methyl)amino]piperidine-1-carboxylate (310 mg, 1.29 mmol) was dissolved in 4M HCl in dioxane solution (3 ml) and stirred at room temperature for 16 h after which the solvent was evaporated and the compound purified by preparative HPLC to afford the title compound as a beige powder (13 mg, 14%). LC-MS 100%, 2.41 min (7 minute LC-MS method), m/z=438.1/439.8, 1H NMR (500 MHz, Methanol-d4) δ 7.12 (s, 1H), 6.11 (s, 1H), 4.46 (s, 2H), 4.01-3.81 (m, 1H), 3.45 (d, J=12.9 Hz, 2H), 3.12-2.97 (m, 2H), 2.82 (s, 3H), 2.35 (s, 3H), 2.22 (s, 3H), 2.13-1.93 (m, 4H).

Workup

  1. customwas evaporated
  2. customthe compound purified by preparative HPLC

Sources & evidence

ORD record
ord-50062bfe31784626bb9d9c951ac10227
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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