Piperidine → HCID 178521524, compound

HRID 1931397Notes

Reaction equation

HRID 1931397 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:15]=[C:16]([S:19][CH2:20][C:21]([OH:23])=O)[NH:17][CH:18]=2)[CH:9]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N:24]1([C:21](=[O:23])[CH2:20][S:19][C:16]2[NH:17][CH:18]=[C:14]([C:10]3[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=3)[N:15]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525686HCID 178525686, compound

Product 1

HCID 178521524HCID 178521524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 mg (0.069 mmol) of (4-(pyridin-3-yl)-1H-imidazol-2-ylsulfanyl)-acetic acid trifluoroacetic acid salt from step (b), 8.8 mg (0.1 mmol) of piperidine, 24.9 mg (0.076 mmol) TOTU and 15.9 mg (0.138 mmol) NEM in 4 ml of DMF were stirred at room temperature for 4 h. After evaporation, water and dichloromethane were added, the organic phase was separated, washed with water, dried, evaporated, and the product was purified by RP18 chromatography. Yield: 7 mg.

Workup

  1. customAfter evaporation, water and dichloromethane
  2. additionwere added
  3. customthe organic phase was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customthe product was purified by RP18 chromatography

Sources & evidence

ORD record
ord-11e0df71b1b7440092bad356fec86e1e
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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