Trifluoroacetic acid → HCID 18536068, compound

HRID 412136Notes

Reaction equation

HRID 412136 reaction equation
Cl.C([O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[N:34]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[C:38]([F:44])[CH:37]=4)[CH:33]=[N:32][CH:31]=3)[CH2:25][C:24]2=[O:45])[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[H][H]>CO.CCOC(C)=O.[Pd]>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[OH:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[N:34]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[C:38]([F:44])[CH:37]=4)[CH:33]=[N:32][CH:31]=3)[CH2:25][C:24]2=[O:45])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18536088HCID 18536088, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18536068HCID 18536068, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of the crude product from Step F (ca 1.68 mmol) in 25 mL of 1:1 MeOH/EtOAc was added trifluoroacetic acid (0.10 mL) and 10% palladium on carbon (800 mg). The solution was stirred under a balloon atmosphere of hydrogen at room temperature. After 4 hours, the solution was filtered through celite, the filter pad was rinsed with 1:1 MeOH/THF, and the filtrate was concentrated in vacuo. The crude material containing the titled product was used in the next reaction without further purification.

Workup

  1. filtrationthe solution was filtered through celite
  2. washthe filter pad was rinsed with 1:1 MeOH/THF
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe crude material containing the titled product
  5. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-654fe8cba9e147e88ccfa04be1dc7804
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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