HCID 59749538, compound → HCID 11528976, compound

HRID 747278Notes

Reaction equation

HRID 747278 reaction equation
COC1C=CC(C[S:8][C:9]2[NH:13][C:12]([CH:14]([C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)[CH3:15])=[CH:11][N:10]=2)=CC=1>FC(F)(F)C(O)=O>[N:21]1[C:22]2[C:17](=[C:16]([CH:14]([C:12]3[NH:13][C:9](=[S:8])[NH:10][CH:11]=3)[CH3:15])[CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 59749538HCID 59749538, compound2×

Product 1

HCID 11528976HCID 11528976, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-{1-[2-(4-Methoxy-benzylsulfanyl)-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E6) (3 g, 8.0 mmol) and trifluoroacetic acid (100 mL) in a resealable tube was heated to 115° C. for 1 h 20 m. The mixture was cooled to rt and TFA removed under vacuum. The residual acid was quenched with NH3-MeOH. The residue was evaporated and resolvated with 3:1 chloroform:isopropanol (500 mL). The organic solution was washed with water (3×40 mL) and brine (1×30 mL). The solution was dried over MgSO4, filtered, and evaporated to leave a solid. This material was purified on a short column of silica gel by gradient elution with 3 to 9% NH3-MeOH:CH2Cl2 to give 4-(1-quinolin-5-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 7) 1.44 g (71%).

Workup

  1. customTFA removed under vacuum
  2. customThe residual acid was quenched with NH3-MeOH
  3. customThe residue was evaporated
  4. washThe organic solution was washed with water (3×40 mL) and brine (1×30 mL)
  5. dry with materialThe solution was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid
  9. customThis material was purified on a short column of silica gel by gradient elution with 3 to 9% NH3-MeOH

Sources & evidence

ORD record
ord-a54eccb1b2aa4cca91969eba2b420566
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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