Reaction equation
[NH2:1][C:2]1[C:3]([C:7]([OH:9])=O)=[N:4][S:5][N:6]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[F:18])[NH2:14].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.[Cl-].[Na+].O.Cl>[NH2:1][C:2]1[C:3]([C:7]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([F:18])=[C:11]([Br:10])[CH:12]=2)=[O:9])=[N:4][S:5][N:6]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 4-amino-1,2,5-thiadiazole-3-carboxylic acid (250 mg, 1.7 mmol) and 3-bromo-4-fluoroaniline (393 mg, 2.1 mmol) in N,N-dimethylformamide (5 mL) was treated with O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (784 mg, 2.1 mmol) followed by N,N-diisopropylethylamine (0.36 mL, 2.1 mmol) and stirred for 16 h. The reaction mixture was diluted with brine (50 mL) and 0.1 N HCl (100 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated. Purification of the crude reaction mixture on silica gel gave the desired product (414 mg, 76%). LCMS for C9H7BrFN4OS(M+H)+: m/z=316.9, 318.8.
Workup
- extractionextracted with ethyl acetate (2×150 mL)
- washThe combined organic extracts were washed with brine (50 mL)
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification of the crude
- customreaction mixture on silica gel
Sources & evidence
- ORD record
- ord-3787938b02ad40539dce4a9fc3ff1d74
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372870B2
Linked notes
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