2-Aminothiazole → HCID 178527553, compound

HRID 559498Notes

Reaction equation

HRID 559498 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][C:6]1[N:10](COC)[C:9]([C:14]2[CH:19]=[CH:18][C:17](S[Si](C(C)C)(C(C)C)C(C)C)=[CH:16][CH:15]=2)=[N:8][N:7]=1.[N+]([O-])([O-])=O.[K+].[S:39](Cl)(Cl)(=[O:41])=[O:40].[S:44]1[CH:48]=[CH:47][N:46]=[C:45]1[NH2:49]>C(#N)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][C:6]1[NH:10][C:9]([C:14]2[CH:15]=[CH:16][C:17]([S:39]([NH:49][C:45]3[S:44][CH:48]=[CH:47][N:46]=3)(=[O:41])=[O:40])=[CH:18][CH:19]=2)=[N:8][N:7]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 24434Potassium NitrateHCID 24648Sulfuryl chlorideHCID 67001330HCID 67001330, compound

Product 1

HCID 178527553HCID 178527553, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(3-chloro-benzyl)-4-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-4H-[1,2,4]triazole (0.42 mmol) in acetonitrile (5 mL) at 0° C. was added potassium nitrate (1.05 mmol) and sulfuryl chloride, and the mixture was stirred for 1 h. The inorganic precipitate was filtered and washed with acetonitrile. The organic phase was concentrated and the residue was dissolved in THF (1.3 mL). To the solution were added thiazol-2-ylamine (0.5 mmol) and excess pyridine. The mixture was stirred over weekend. After concentration, the residue in 6N HCl (1 mL) and ethanol (1 mL) was stirred at 80° C. for 16 h before the reaction mixture was concentrated, the crude product was purified by reverse phase HPLC to give 4-[5-(3-chloro-benzyl)-4H-[1,2,4]triazol-3-yl]-N-thiazol-2-yl-benzenesulfonamide (0.1 mmol).

Workup

  1. filtrationThe inorganic precipitate was filtered
  2. washwashed with acetonitrile
  3. concentrationThe organic phase was concentrated
  4. dissolutionthe residue was dissolved in THF (1.3 mL)
  5. stirringThe mixture was stirred over weekend
  6. concentrationAfter concentration
  7. stirringthe residue in 6N HCl (1 mL) and ethanol (1 mL) was stirred at 80° C. for 16 h before the reaction mixture
  8. concentrationwas concentrated
  9. customthe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-db249b8e231b4632b00c665474cda1bf
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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