HCID 178522909, compound → HCID 178522910, compound

HRID 2289971Notes

Reaction equation

HRID 2289971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:23]#[C:24][CH2:25][OH:26])=[CH:17][C:16]=3[F:27])=[O:11])=[CH:4][CH:3]=1>C(Cl)Cl.CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:17][C:16]=3[F:27])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178522909HCID 178522909, compound

Product 1

HCID 178522910HCID 178522910, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A suspension of the title compound of Example 53 (0.300 g) and 10% Pd/C (0.03 g) in 25 mL of 3:1 CH2Cl2 /MeOH is hydrogenated at atmospheric pressure overnight. The reaction is filtered through celite. The filtrate is condensed. The crude product is recrystallized from EtOAc/hexanes to yield 0.200 g of the desired product as a pale-yellow solid.

Workup

  1. customis hydrogenated at atmospheric pressure overnight
  2. filtrationThe reaction is filtered through celite
  3. customcondensed
  4. customThe crude product is recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-d72ae011d3fd48b2a4a5841b3ebf6c96
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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