Hydrochloric Acid → HCID 117839733, compound

HRID 1477732Notes

Reaction equation

HRID 1477732 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3([CH2:18][O:17]C[O:15][CH2:14]3)[CH2:12][N:11]([C:19]3[N:24]=[C:23]([CH3:25])[N:22]([CH2:26][C:27]4[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=4)[C:21](=[O:36])[N:20]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:19]3[N:24]=[C:23]([CH3:25])[N:22]([CH2:26][C:27]4[S:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=4)[C:21](=[O:36])[N:20]=3)[CH2:12][C:13]2([CH2:18][OH:17])[CH2:14][OH:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 117839848HCID 117839848, compound

Product 1

HCID 117839733HCID 117839733, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane solution (500 μL) of 4-[11-(4-fluorophenyl)-2,4-dioxa-8-azaspiro[5.5]undecan-8-yl]-6-methyl-1-{[5-(trifluoro methyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (5.00 mg, 9.53 μmol) synthesized in Reference Synthesis Example 363, 12 M hydrochloric acid (500 μL) was added and the resultant mixture was stirred at 110° C. for 2 hours. To the resultant reaction solution, 12 M hydrochloric acid (500 μL) was added and the resultant mixture was stirred at 110° C. for 2.5 hours. After the completion of the reaction, to the reaction solution, saturated sodium carbonate aqueous solution was added and extraction with chloroform from the reaction solution was performed. The organic layer was dried over anhydrous sodium sulfate and was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0→20/1) to obtain the title compound (1.59 mg, yield: 33%).

Workup

  1. additionwas added
  2. additionwas added
  3. customAfter the completion of the reaction
  4. extractionextraction with chloroform from the reaction solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customthe resultant residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0→20/1)

Sources & evidence

ORD record
ord-6f2f7b46361f4066a5c5ad6cadfdcb82
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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