Trifluoroacetic acid → HCID 178420122, compound

HRID 1174667Notes

Reaction equation

HRID 1174667 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([C:10]([C:12]3[N:13]=[CH:14][N:15](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:16]=3)=O)=[CH:7][CH:8]=[CH:9][C:2]=12.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:15]1[CH:16]=[C:12]([CH2:10][C:6]2[C:3]3=[N:4][S:5][N:1]=[C:2]3[CH:9]=[CH:8][CH:7]=2)[N:13]=[CH:14]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59749576benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone

Product 1

HCID 178420122HCID 178420122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate L3) (500 mg, 1.12 mmol) in methylene chloride (2 mL) was treated with triethylsilane (8 mL), and trifluoroacetic acid (8 mL) at rt for 48 h. This mixture was evaporated under vacuum and quenched with a ˜7M NH3-MeOH solution. The solvent was exchanged with CH2Cl2. The solution was concentrated onto silica gel and purified by chromatography, eluting with 3% NH3-MeOH:CH2Cl2 to give 4-(1H-imidazol-4-ylmethyl)-benzo[1,2,5]thiadiazole (Intermediate L4). 4-(1H-imidazol-4-ylmethyl)-benzo[1,2,5]thiadiazole (Intermediate L4) was subjected to the appropriate process steps in Method A to produce 4-benzo[1,2,5]thiadiazol-4-ylmethyl-1,3-dihydro-imidazole-2-thione (Compound 16).

Workup

  1. customThis mixture was evaporated under vacuum
  2. customquenched with a ˜7M NH3-MeOH solution
  3. concentrationThe solution was concentrated onto silica gel
  4. custompurified by chromatography
  5. washeluting with 3% NH3-MeOH

Sources & evidence

ORD record
ord-418600f229bf4b259d9431b1fc21da84
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

Loading…