Trifluoroacetic acid → HCID 178420122, compound

HRID 747259Notes

Reaction equation

HRID 747259 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-8811cdac01ae48c58ecf1a519ed95e3c
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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