3-(Pyridin-2-yloxy)propan-1-amine → 2-tert-Butyl-5-phenyl-4-{[3-(pyridin-2-yloxy)propyl]amino}isothiazol-3(2H)-one 1,1-dioxide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][CH2:10][NH2:11].[C:12]([N:16]1[C:20](=[O:21])[C:19](Cl)=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:17]1(=[O:30])=[O:29])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([N:16]1[C:20](=[O:21])[C:19]([NH:11][CH2:10][CH2:9][CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:17]1(=[O:29])=[O:30])([CH3:15])([CH3:13])[CH3:14]Participants
Procedure
The title compound was prepared as described for Example 24 from 1 equivalent of [3-(pyridin-2-yloxy)propyl]amine, 2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 1 equivalent TEA with a reaction time of 30 mins. The residue was purified by silica gel column chromatography (Horizons Biotage) using 5:1 petroleum ether 40-60° C. in EtOAc as eluent to give the title compound (0.178 g, 65%) as a solid. 1H NMR (500 MHz CDCl3): δ 8.17 (dd, 1H), 7.62-7.57 (m, 1H), 7.54-7.48 (m, 2H), 7.45-7.40 (m, 3H), 6.91-6.88 (m, 1H), 6.74 (d, 1H), 6.00 (t, 1H), 4.28 (t, 2H), 3.04 (q, 2H), 1.83 (quintet, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 163.8, 159.9, 147.0, 138.9, 135.5, 131.8, 129.7, 128.8, 125.4, 117.3, 111.5, 106.9, 63.6, 61.6, 42.0, 28.9, 27.9; Mass Spectrum: M+H+ 416.
Workup
- customThe title compound was prepared
- customThe residue was purified by silica gel column chromatography (Horizons Biotage)
- custom5:1 petroleum ether 40-60° C. in EtOAc
Sources & evidence
- ORD record
- ord-4efd3eac724b45839414f26e5bfa7794
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723333B2
Reaction notes
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