Hydrochloric Acid → 4-tert-Butyl-N-(2-methyl-3-(5-(6-morpholinopyridazin-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)benzamide

HRID 1174564Notes

Reaction equation

HRID 1174564 reaction equation
[C:1]([C:5]1[CH:41]=[CH:40][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[N:20][C:21]([O:37]C)=[C:22]([NH:24][C:25]4[N:26]=[N:27][C:28]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:29][CH:30]=4)[CH:23]=3)[C:13]=2[CH3:39])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.Cl.[OH-].[Na+]>O>[C:1]([C:5]1[CH:41]=[CH:40][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:26]=[N:27][C:28]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:29][CH:30]=4)[C:21](=[O:37])[NH:20][CH:19]=3)[C:13]=2[CH3:39])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 595578954-tert-Butyl-N-(3-(6-methoxy-5-(6-morpholinopyridazin-3-ylamino)pyridin-3-yl)-2-methylphenyl)benzamide

Product 1

HCID 249679844-tert-Butyl-N-(2-methyl-3-(5-(6-morpholinopyridazin-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)benzamideYield 41.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 25-mL round-bottomed flask equipped with a magnetic stirrer was charged with 4-tert-butyl-N-(3-(6-methoxy-5-(6-morpholinopyridazin-3-ylamino)pyridin-3-yl)-2-methylphenyl)benzamide (7) (0.10 g, 0.18 mmol), dioxane (3 mL), H2O (1 mL), and conc. HCl (0.3 mL). After the reaction mixture was refluxed for 2 h, it was basified with 10 N NaOH (1 mL). The mixture was then diluted with water (5 mL), extracted with dichloromethane (3×5 mL), washed with H2O (5 mL) and brine (5 mL), dried over sodium sulfate, and concentrated in vacuo. The crude mixture was purified by column chromatography, gradient 0-33% MeOH in dichloromethane, to afford 0.040 g (41%) of 4-tert-butyl-N-(2-methyl-3-(5-(6-morpholinopyridazin-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)benzamide (8) as a solid: LCMS m/z 552.2342 (M+).

Workup

  1. customA 25-mL round-bottomed flask equipped with a magnetic stirrer
  2. temperatureAfter the reaction mixture was refluxed for 2 h
  3. extractionextracted with dichloromethane (3×5 mL)
  4. washwashed with H2O (5 mL) and brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by column chromatography, gradient 0-33% MeOH in dichloromethane

Sources & evidence

ORD record
ord-be053bc9fb104d98b75732cbfd6029ae
Source dataset
uspto-grants-2010_11
Patent number
US07838523B2

Reaction notes

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