Sodium Chloride → HCID 117840015, compound

HRID 1477729Notes

Reaction equation

HRID 1477729 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([OH:14])[CH2:12][N:11]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[Cu](C#N)C#N.[Cl-].[Na+].CN(C)[CH:41]=[O:42]>>[CH:41]([O:14][CH:13]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:9][CH2:10][N:11]([C:15]2[N:20]=[CH:19][N:18]([CH2:21][C:22]3[S:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=3)[C:17](=[O:31])[N:16]=2)[CH2:12]1)=[O:42]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 78166221HCID 78166221, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 117840015HCID 117840015, compoundYield 2%

Procedure

To a crude product synthesized using 4-[4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (50.0 mg, 0.111 mmol) synthesized in Synthesis Example 190 in a similar manner to Reference Synthesis Example 68, N,N-dimethylformamide (1.0 mL) and copper cyanide (49.3 mg, 0.550 mmol) were added and the resultant mixture was stirred at 100° C. for 1 day. After the completion of the reaction, to the reaction solution, saturated sodium chloride aqueous solution was added and extraction with ethyl acetate 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 (hexane/ethyl acetate=1/1→0/1) to obtain the title compound (0.8 mg, yield: 2%).

Workup

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

Sources & evidence

ORD record
ord-cdce4f97029a4a638185e77a3f1ab865
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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