Methanol → HCID 59636276, compound

HRID 2383859Notes

Reaction equation

HRID 2383859 reaction equation
Cl[C:2]1[C:7]2[C:8]([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])=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CO>C(O)(=O)C.C(Cl)Cl.[Zn]>[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:8]2[C:7]3[CH:2]=[N:3][CH:4]=[CH:5][C:6]=3[S:10][CH:9]=2)[C:12]1=[O:23]

Participants

6

Reactant 2

HCID 887MethanolHCID 498722521-(4-Chloro-thieno[3,2-c]pyridin-3-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 59636276HCID 59636276, compoundYield 40.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Activated Zinc (417 mg, 6.380 mmol) was added to a stirred solution of 1-(4-chloro-thieno[3,2-c]pyridin-3-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-136a: 220 mg, 0.6380 mmol) in acetic acid (10 mL). The resulting mixture was stirred at room temperature for 2 days. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Aqueous NH3 solution was added to the concentrate and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (5% MeOH in DCM) afforded 80 mg of the product (40.6% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionAqueous NH3 solution was added to the
  4. concentrationconcentrate
  5. extractionextracted with DCM
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customPurification by column chromatography on silica gel (5% MeOH in DCM)

Sources & evidence

ORD record
ord-bb2ba929d53b4fac8d2862145db13e09
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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