Acetate → HCID 21866534, compound

HRID 1582916Notes

Reaction equation

HRID 1582916 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:19](=S)[NH2:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].IC.C([O-])(=O)C.[NH4+:28].C([O-])(=O)C>ClCCl>[C:19]([C:12]1[S:11][C:10]([CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[N:14][C:13]=1[C:15]([F:18])([F:17])[F:16])(=[NH:20])[NH2:28]

Participants

6

Reactant 4

HCID 175AcetateHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 21866462HCID 21866462, compound

Product 1

HCID 21866534HCID 21866534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(N-BOC-Aminomethyl)-4-trifluoromethylthiazole-5-thioamide [sic] (2.5 g, 7.32 mmol) was dissolved in dichloromethane (10 ml), and iodomethane (10.4 g, 73.24 mmol) was added. Then, the mixture was stirred for 48 hours at room temperature. After the solvent had been removed on a rotary evaporator, the residue was taken up in methanol (5 ml), and 10% strength methanolic ammonium acetate solution (8.5 ml, 10.98 mmol) was added. After the mixture had been stirred for 4 days at room temperature, the solution of the crude product was passed over an acetate-loaded ion exchanger and the solvent was removed on a rotary evaporator. The crude product was purified by flash chromatography. Yield: 0.8 g (2.08 mmol, 28%).

Workup

  1. customAfter the solvent had been removed on a rotary evaporator
  2. stirringAfter the mixture had been stirred for 4 days at room temperature
  3. customthe solvent was removed on a rotary evaporator
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-142499e2277749a2a89ad6e28db6cb9b
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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