Methanesulfonyl chloride → 5-(Azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole

HRID 1851718Notes

Reaction equation

HRID 1851718 reaction equation
C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[CH3:15][O:16][CH2:17][C:18]1[S:22][C:21]2=[N:23][C:24]([C:28]([F:31])([F:30])[F:29])=[C:25]([CH2:26]O)[N:20]2[N:19]=1.[N-:32]=[N+:33]=[N-:34].[Na+]>ClCCl.CN(C=O)C.C(OCC)C.O>[N:32]([CH2:26][C:25]1[N:20]2[C:21]([S:22][C:18]([CH2:17][O:16][CH3:15])=[N:19]2)=[N:23][C:24]=1[C:28]([F:31])([F:30])[F:29])=[N+:33]=[N-:34]

Participants

9

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 70976689HCID 70976689, compound

Product 1

HCID 709767325-(Azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazoleYield 100%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (3.22 g, 24.88 mmol, 5 eq) and methanesulfonyl chloride (0.855 g, 7.47 mmol, 1.5 eq) are successively and slowly added at 0° C. to a solution of [2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol a3 (1.33 g, 4.98 mmol, 1 eq) in dichloromethane (30 ml). Sodium azide (0.485 g, 7.47 mmol, 1.5 eq) in suspension in DMF (5 ml) is added at 0° C., then warmed up to room temperature and the reaction mixture is stirred overnight. After hydrolysis (H2O) and extraction with diethylether, the combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure to afford 1.45 g of 5-(azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a18.

Workup

  1. dry with materialthe combined organic layers are dried over MgSO4
  2. filtrationfiltered
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6a748073cf064108b8d6be4e9c0454df
Source dataset
uspto-grants-2015_02
Patent number
US08957218B2

Reaction notes

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