Pyridine → HCID 77768044, compound

HRID 2230323Notes

Reaction equation

HRID 2230323 reaction equation
[C:1]([NH:5][C:6]([CH:8]([NH:24][C:25]([CH:27]([NH:32][C:33]([N:35]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1>C1COCC1.[Pd]>[C:1]([NH:5][C:6]([CH:8]([NH:24][C:25]([CH:27]([NH:32][C:33]([N:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1)=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:15]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 1049PyridineHCID 77768281HCID 77768281, compound

Product 1

HCID 77768044HCID 77768044, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 134 (0.178 g, 0.32 mmol) in 15 mL of THF was added 5% Pd/C (0.02 g) and 1 mL of pyridine. The mixture was subjected to hydrogenation for 15.5 hours at 20 psi. The crude reaction mixture was evaporated to dryness and purified by chromatography (silica gel, 50% ethyl acetate/hexane). The product was further purified by crystallizing from petroleum ether and toluene to give the title compound (0.089 g, 50%) as a white solid, mp 95-96° C.

Workup

  1. customThe crude reaction mixture
  2. customwas evaporated to dryness
  3. custompurified by chromatography (silica gel, 50% ethyl acetate/hexane)
  4. customThe product was further purified
  5. customby crystallizing from petroleum ether and toluene

Sources & evidence

ORD record
ord-e995effe1b544c03852d293c76c2e7d4
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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