Triphenylphosphine → 1-[2-(Methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanamine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[N:31]2[C:27]([S:28][C:29]([CH2:32][O:33][CH3:34])=[N:30]2)=[N:26][C:25]=1[C:35]([F:38])([F:37])[F:36])=[N+]=[N-]>C1COCC1.O>[CH3:34][O:33][CH2:32][C:29]1[S:28][C:27]2=[N:26][C:25]([C:35]([F:38])([F:36])[F:37])=[C:24]([CH2:23][NH2:20])[N:31]2[N:30]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Triphenylphosphine (1.31 g, 4.98 mmol, 1 eq) is added at room temperature to a suspension of 5-(azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a18 (1.45 g, 4.98 mmol, 1 eq) in THF/H2O (18 ml/2 ml). The reaction mixture is stirred at room temperature for 60 h. The solvent is evaporated under reduced pressure, water is added to the residue, the solution is acidified to pH 2 with aqueous 5N HCl, then extracted with Et2O (1×50 ml). The aqueous layer is basified (pH 8) by addition of a Na2CO3 aqueous solution, and extracted with dichloromethane (2×50 ml), the cumulated organics layers are dried over MgSO4, filtered and evaporated under reduced pressure to afford 1-[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanamine a19.
Workup
- customThe solvent is evaporated under reduced pressure, water
- additionis added to the residue
- extractionextracted with Et2O (1×50 ml)
- additionby addition of a Na2CO3 aqueous solution
- extractionextracted with dichloromethane (2×50 ml)
- dry with materialthe cumulated organics layers are dried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-f84b501b64404af7ad1e70bd3e4b007b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957218B2
Reaction notes
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