2-Aminothiazole → 5-(2-Methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-YL)naphthalene-2-sulfonamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([S:23](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:25])=[O:24])=[CH:18]2.[S:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH2:43].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([S:23]([NH:43][C:39]1[S:38][CH:42]=[CH:41][N:40]=1)(=[O:25])=[O:24])=[CH:18]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A vial was charged with perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate (77.62 mg, 0.142 mmol), THF (1415 μl), and thiazol-2-amine (21.26 mg, 0.212 mmol). The vial was cooled in an ice bath for 5 min, then lithium bis(trimethylsilyl)amide (1M in THF) (354 μl, 0.354 mmol) was added dropwise over 1 min. LC/MS after 5 min showed mostly the desired product. After a total of 20 min, the reaction was quenched by the addition of acetic acid (0.1 mL). The resulting mixture was warmed to room temperature and concentrated. The product was purified by chromatography on silica gel (0 to 5% MeOH/DCM) to give 5-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (59.52 mg, 0.128 mmol) as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.79 (br. s., 1H), 8.51 (d, J=1.9 Hz, 1H), 8.21 (d, J=8.3 Hz, 1H), 7.81-7.65 (m, 2H), 7.57-7.41 (m, 5H), 7.26 (d, J=4.6 Hz, 1H), 6.84 (d, J=4.6 Hz, 1H), 3.73 (s, 3H); m/z (ESI) 465.0 (M+H)+.
Workup
- temperatureThe vial was cooled in an ice bath for 5 min
Sources & evidence
- ORD record
- ord-6908b931324d4a719b099a233034e994
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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