Phenylacetic Acid → HCID 87551058, compound

HRID 1895977Notes

Reaction equation

HRID 1895977 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N=C=N.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH:23]=[C:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:16]=1>C(Cl)Cl>[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][CH:23]=[C:24]2[CH2:25][CH2:26][N:27]([C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:28][CH2:29]2)[N:16]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 160435CarbodiimideHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87551058HCID 87551058, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of phenylacetic acid (61.5 mg, 0.452 mmol) in 10 mL di CH2Cl2 was added PS-carbodiimide 1.25 mmol/g (480 mg, 0.6 mmol), while gently stirring at r.t. After 20 min., the Compound of Example 3 (64 mg, 0.301 mmol) was added. A very slow stirring was maintained overnight. Filtration, followed by washing the resin with CH2Cl2 and evaporation afforded a crude which was purified by flash chromatography (CHCl3-1.4 N MeOH/NH3 100:0.2) yielding the title product (80 mg).

Workup

  1. stirringA very slow stirring
  2. temperaturewas maintained overnight
  3. filtrationFiltration
  4. washby washing the resin
  5. customwith CH2Cl2 and evaporation
  6. customafforded a crude which
  7. customwas purified by flash chromatography (CHCl3-1.4 N MeOH/NH3 100:0.2)

Sources & evidence

ORD record
ord-01022a68b7c542e78efdcf79e98cb51b
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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