2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide → HCID 86645163, compound

HRID 2239689Notes

Reaction equation

[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[Cl:22][C:23]1[N:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>CN(C=O)C>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:35][CH:32]2[CH2:33][CH2:34][N:29]([C:26]3[CH:27]=[N:28][C:23]([Cl:22])=[CH:24][CH:25]=3)[CH2:30][CH2:31]2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.175 g, 0.58 mmol), 1-(6-chloropyridin-3-yl)piperidin-4-amine dihydrochloride (0.196 g, 0.69 mmol) and TEA (0.23 g, 2.31 mmol) was dissolved in dry DMF (3 ml) and heated in a microwave reactor at 130° C. for 30 mins. The reaction mixture was purified with preparative HPLC giving the title compound (0.022 g, 8%). 1H NMR (500 MHz, CDCl3): δ 7.92-7.87 (m, 1H), 7.55-7.48 (m, 2H), 7.48-7.41 (m, 3H), 7.13-7.03 (m, 2H), 5.24-5.18 (m, 1H), 3.45-3.35 (m, 2H), 3.13-3.01 (m, 1H), 2.39-2.29 (m, 2H), 1.82-1.71 (m, 2H), 1.73 (s, 9H), 1.52-1.40 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 159.8, 145.8, 141.7, 138.0, 134.1, 131.8, 130.2, 129.0, 126.6, 125.3, 124.1, 107.5, 61.9, 49.8, 47.8, 32.0, 27.8; Mass Spectrum: M−H+ 475.

Workup

customThe reaction mixture was purified with preparative HPLC

Sources & evidence

ORD record: ord-8c285f70ec3f45ea98e7440dcd3c8b6d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723333B2

Reaction notes

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