Pyridine → HCID 87998464, compound

HRID 2180230Notes

Reaction equation

HRID 2180230 reaction equation
[CH:1]1([CH2:7][C@@H:8]([NH:15]C(=O)OC(C)(C)C)[CH:9]([OH:14])[C:10]([NH:12][NH2:13])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1>C(O)C>[NH2:15][C@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH:9]([OH:14])[C:10]([NH:12]/[N:13]=[CH:34]/[C:33]1[CH:36]=[CH:37][C:30]([Cl:29])=[CH:31][CH:32]=1)=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 77264-ChlorobenzaldehydeHCID 91543769HCID 91543769, compound

Product 1

HCID 87998464HCID 87998464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Example 14A (0.064 g, 0.20 mmol) in ethanol (3 mL) was treated with pyridine (2 mL) and 4-chlorobenzaldehyde (0.033 mL, 0.23 mmol), heated to 85° C., stirred for 16 hours, and concentrated. The concentrate was purified by flash column chormatography on silica gel with ethyl acetate in hexanes, and the purified concntrate was treated with 4N HCl in dioxane, stirred for 4 hours, concentrated, precipitated from diethyl ether, and collected by filtration to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chormatography on silica gel with ethyl acetate in hexanes
  3. additionthe purified concntrate was treated with 4N HCl in dioxane
  4. stirringstirred for 4 hours
  5. concentrationconcentrated
  6. customprecipitated from diethyl ether
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1c1c6e6a00134eb88589eb31b5230e77
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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