1,4-Dioxane hydrochloride → 5-chloro-N-((2,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yl)methyl)-2-methyl-3-(piperidin-4-yloxy)benzamide

HRID 1050466Notes

Reaction equation

HRID 1050466 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23](=[O:35])[NH:24][CH2:25][C:26]2[C:31](=[O:32])[CH:30]=[C:29]([CH3:33])[NH:28][C:27]=2[CH3:34])[C:5]([CH3:22])=[C:6]([CH:21]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.Cl.O1CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:21]=[C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]([CH3:22])=[C:4]([CH:3]=1)[C:23]([NH:24][CH2:25][C:26]1[C:31](=[O:32])[CH:30]=[C:29]([CH3:33])[NH:28][C:27]=1[CH3:34])=[O:35]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 76902143Tert-butyl 4-(5-chloro-3-(((2,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenoxy)piperidine-1-carboxylate

Product 1

HCID 769023325-chloro-N-((2,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yl)methyl)-2-methyl-3-(piperidin-4-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(5-chloro-3-(((2,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yl)methyl)carbamoyl)-2-methylphenoxy)piperidine-1-carboxylate (80 mg, 158 mmol) in DCM (2 mL) was treated with 4 M HCl/dioxane (2 mL). The reaction stirred for 2 h at RT, then was concentrated in vacuo and triturated with EtOAc to give 5-chloro-N-((2,6-dimethyl-4-oxo-1,4-dihydropyridin-3-yl)methyl)-2-methyl-3-(piperidin-4-yloxy)benzamide as the hydrogen chloride salt (0.050 g, 113 mmol, 72% yield). 1H NMR (400 MHz, DMSO-d6) δ 1.74-1.90 (m, 2 H) 2.07 (s, 3 H) 2.11 (d, J=4.80 Hz, 2 H) 2.57 (s, 3 H) 2.72 (s, 3 H) 3.09 (br. s., 2 H) 3.17 (s, 2 H) 4.38 (d, J=4.80 Hz, 2 H) 4.60-4.87 (m, 1 H) 6.89 (s, 1 H) 7.12 (s, 1 H) 7.23 (d, J=1.77 Hz, 1 H) 8.69 (t, J=5.05 Hz, 1 H) 8.98 (br. s., 2 H) 14.42 (br. s., 1 H). MS(ES) [M+H]+ 404.3.

Workup

  1. concentrationwas concentrated in vacuo
  2. customtriturated with EtOAc

Sources & evidence

ORD record
ord-1d1ed34d3de040c091c4eac98b70ac18
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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