Hydrochloric Acid → HCID 117839848, compound

HRID 1477687Notes

Reaction equation

HRID 1477687 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[C:18]([CH3:20])[N:17]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:16](=[O:31])[N:15]=3)[CH2:10][C:9]2([CH2:37][O:38][CH2:39][O:40]C)[CH2:32]OCOC)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3([CH2:32][O:40][CH2:39][O:38][CH2:37]3)[CH2:10][N:11]([C:14]3[N:19]=[C:18]([CH3:20])[N:17]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:16](=[O:31])[N:15]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117839159HCID 117839159, compoundHCID 131736497HCID 131736497, compound

Product 1

HCID 117839848HCID 117839848, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane solution (600 μL) of 4-{4-(4-fluorophenyl)-3,3-bis[(methoxymethoxy)methyl]piperidin-1-yl}-6-methyl-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (10.0 mg, 16.6 μmol) synthesized in Reference Synthesis Example 362, 12 M hydrochloric acid (200 μL) was added and the resultant mixture was stirred at 60° C. for 2 hours. To saturated sodium carbonate-chloroform solution, the reaction solution was added dropwise and extraction from the resultant mixture with chloroform was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/4→0/1) to obtain the title compound (6.60 mg, yield 76%).

Workup

  1. additionwas added
  2. extractionextraction from the resultant mixture with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/4→0/1)

Sources & evidence

ORD record
ord-f9cffeb57586422ca655e98cf21d9a8d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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