1,4-Dioxane hydrochloride → HCID 68432000, compound

HRID 2092125Notes

Reaction equation

HRID 2092125 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([C:15]2[CH:16]=[N:17][N:18](COCC[Si](C)(C)C)[CH:19]=2)[CH3:14])=[O:11])[N:5]=[CH:4][C:3]=1[NH:28][C@@H:29]1[CH2:34][C@@H:33]2[CH2:35][C@@H:31]([C:32]2([CH3:37])[CH3:36])[C@H:30]1[CH3:38].Cl.O1CCOCC1>>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([C:15]2[CH:19]=[N:18][NH:17][CH:16]=2)[CH3:14])=[O:11])[N:5]=[CH:4][C:3]=1[NH:28][C@@H:29]1[CH2:34][C@@H:33]2[CH2:35][C@@H:31]([C:32]2([CH3:36])[CH3:37])[C@H:30]1[CH3:38]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68429614HCID 68429614, compound

Product 1

HCID 68432000HCID 68432000, compoundYield 12%

Conditions

Temperature
100 °C

Procedure

2-(5-Chloro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl)-N-[1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)ethyl]acetamide (56.2 mg, 0.10 mmol) was mixed with 4 M hydrogen chloride/1,4-dioxane (2 mL) and stirred at 100° C. for 5 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/MeOH=20/1) to give the desired product (5.2 mg, 12% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/MeOH=20/1)

Sources & evidence

ORD record
ord-d7adffeedf5a427bb75aeec105de63b9
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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