HCID 71000688, compound → HCID 69081573, compound

HRID 1023455Notes

Reaction equation

HRID 1023455 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=2)=[C:4]([CH3:20])[CH:3]=1.[H][H]>CO.C(Cl)Cl.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=2)=[C:4]([CH3:20])[CH:3]=1

Participants

6

Reactant 2

HCID 71000688HCID 71000688, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69081573HCID 69081573, compoundYield 70.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

[4-(4-Fluoro-2-methyl-phenylethynyl)-pyridin-2-yl]-urea (25 mg, 0.093 mmol) is dissolved in methanol (1.0 mL) and DCM (1.0 mL). Then 5% palladium on carbon (20 mg, 0.0090 mmol) is added. The reaction is stirred for 16 hrs under the hydrogen atmosphere. The palladium on carbon is filtered and the filtrate is concentrated to give the crude product. Methanol (1 mL) is added into the crude and a white solid is formed. The solid is filtered, rinsed with more methanol and dried to give 18 mg of the titled product.

Workup

  1. filtrationThe palladium on carbon is filtered
  2. concentrationthe filtrate is concentrated
  3. customto give the crude product
  4. customa white solid is formed
  5. filtrationThe solid is filtered
  6. washrinsed with more methanol
  7. customdried

Sources & evidence

ORD record
ord-487953f7d2e64fafac075067ece294c6
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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