Trifluoroacetic acid → HCID 70008156, compound

HRID 412138Notes

Reaction equation

HRID 412138 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][C@H:27]([CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])[N:26]([CH2:35][C:36]3[N:40]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[C:44]([F:50])[CH:43]=4)[CH:39]=[N:38][CH:37]=3)[CH2:25][C:24]2=[O:51])[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1.[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[H][H]>CO.CCOC(C)=O.[Pd]>[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[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][C@H:27]([CH2:29][CH2:30][S:31]([CH3:34])(=[O:32])=[O:33])[N:26]([CH2:35][C:36]3[N:40]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[C:44]([F:50])[CH:43]=4)[CH:39]=[N:38][CH:37]=3)[CH2:25][C:24]2=[O:51])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70008919HCID 70008919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70008156HCID 70008156, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of the product from Step D (383 mg, 0.527 mmol) in 10 mL of 1:1 MeOH/EtOAc was added trifluoroacetic acid (0.10 mL) and 10% palladium on carbon (300 mg). The solution was stirred under a balloon atmosphere of hydrogen at room temperature. After 1.5 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-5dd28f55d8d0498c86b8643465e0baaf
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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