HCID 23585763, compound → HCID 23585762, compound

HRID 1868299Notes

Reaction equation

HRID 1868299 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH2:15][CH2:14][CH2:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1>[Pd].CN(C=O)C.CO>[NH2:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 23585763HCID 23585763, compound

Product 1

HCID 23585762HCID 23585762, compoundYield 30.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-amino-2-cyclopent-1-enyl-thieno[3,2-c]pyridine-7-carboxylic acid amide 34 (prepared in example 6 above) (0.056 g, 0.155 mmol) and 10% palladium on carbon (5 mol %) in DMF (1 mL) was stirred under H2 (1 atm) for 20 h. The suspension was diluted with MeOH (10 mL) and filtered. Solvent was removed in vacuo. To the crude solid of 35 was added concentrated H2SO4 (0.25 mL). The purple solution was stirred for 1 h followed by the addition of ice (2 g). The precipitate was filtered then purified by silica gel column chromatography (eluent: 10% MeOH, 1% NH4OH in CH2Cl2) and converted to the HCl salt to afford 12.5 mg of 36. 1H NMR (400 MHz, d6-DMSO) δ 8.76 (s, 2H), 8.45 (s, 1H), 8.29 (s, 1H), 7.75 (m, 3H), 3.37 (m, 1H), 2.14 (m, 2H), 1.72 (m, 6H).

Workup

  1. filtrationfiltered
  2. customSolvent was removed in vacuo
  3. additionTo the crude solid of 35 was added concentrated H2SO4 (0.25 mL)
  4. stirringThe purple solution was stirred for 1 h
  5. additionfollowed by the addition of ice (2 g)
  6. filtrationThe precipitate was filtered
  7. customthen purified by silica gel column chromatography (eluent: 10% MeOH, 1% NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-d9d2fcc5b5ae45028c0b6763645c13b4
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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