1-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one → 1-(4-Methyl-pyridin-3-yl)-3-thieno[3,2-c]pyridin-2-yl-imidazolidin-2-one

HRID 80152Notes

Reaction equation

HRID 80152 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]([N:11]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:21]=4[CH3:22])[C:12]3=[O:23])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1>CO.C(Cl)(Cl)Cl.[Pd]>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:13]1[CH2:14][CH2:15][N:11]([C:9]2[S:10][C:6]3[CH:5]=[CH:4][N:3]=[CH:2][C:7]=3[CH:8]=2)[C:12]1=[O:23]

Participants

5

Reactant 1

HCID 498718701-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 498723541-(4-Methyl-pyridin-3-yl)-3-thieno[3,2-c]pyridin-2-yl-imidazolidin-2-oneYield 14%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

10% Pd-C (10 mg) was added to a solution of 1-(4-chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (98A: 80 mg, 0.232 mmol) in methanol (10 mL) under nitrogen atmosphere. The resulting mixture was hydrogenated at 30 PSI (2.04 atm) for 12 hours at room temperature. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was filtered through celite bed, washed with methanol and the filtrate was concentrated under reduced pressure to afford the crude product. Purification by preparative TLC afforded 10 mg of the product (14% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-4beff4c6ce57447caca5b3131074526c
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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