HCID 58933540, compound → HCID 58933792, compound

HRID 854298Notes

Reaction equation

HRID 854298 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=[O:28])[CH:22]=2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][Mg]Cl>C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH:27]([OH:28])[CH3:29])[CH:22]=2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 58933540HCID 58933540, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58933792HCID 58933792, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-{[(2-formyl-pyridine-4-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (EXAMPLE 166, Step 6) (50 mg, 0.131 mmol) in TBF (2 mL) at −78° C. was added 3.0M methylmagnesium chloride (45 μL, 0.135 mmol). The mixture was stirred for 5 min and allowed to warm to rt. The reaction was diluted with 10% aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (25 mL). The ethyl acetate extract was concentrated and chromatographed on silica using 100% ethyl acetate to ethyl acetate/methanol (95/5) to give the 4-({[2-(1-hydroxy-ethyl)-pyridine-4-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. extractionextracted with ethyl acetate (25 mL)
  2. extractionThe ethyl acetate extract
  3. concentrationwas concentrated
  4. customchromatographed on silica using 100% ethyl acetate to ethyl acetate/methanol (95/5)

Sources & evidence

ORD record
ord-d6f20e8f85a24bf1ae4f21e164013d76
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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