2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide → HCID 67244125, compound

HRID 2422093Notes

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].[F:20][CH:21]([F:35])[O:22][C:23]1[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=1)[CH2:26][NH:27][C:28](=[O:31])[CH2:29][NH2:30]>CN(C=O)C>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:30][CH2:29][C:28]([NH:27][CH2:26][C:25]2[CH:32]=[CH:33][CH:34]=[C:23]([O:22][CH:21]([F:20])[F:35])[CH:24]=2)=[O:31])=[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), N-[3-(difluoromethoxy)benzyl]glycinamide (0.159 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 by preparative HPLC to yield the title compound (0.118 g, 41%). 1H NMR (500 MHz, CDCl3): δ 7.46-7.35 (m, 5H), 7.35-7.28 (m, 1H), 7.09-7.01 (m, 2H), 6.99-6.94 (m, 1H), 6.50 (t, 1H), 6.02-5.94 (m, 1H), 5.91-5.82 (m, 1H), 4.37-4.31 (m, 2H), 3.53-3.48 (m, 2H), 1.71 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 167.3, 159.3, 139.9, 134.9, 131.5, 130.5, 130.2, 129.0, 125.1, 124.5, 119.4, 119.0, 116.0, 113.9, 109.9, 62.0, 46.8, 43.4, 27.8; Mass Spectrum: M−H+ 494.

Workup

customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-fdc131ed847e4c1497b59672ee9f4248
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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