3-(Bromomethyl)-5-methylisoxazole → HCID 67241878, compound

HRID 2422109Notes

Reaction equation

Br[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[C:9]([N:13]1[C:17](=[O:18])[C:16]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[C:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:14]1(=[O:33])=[O:32])([CH3:12])([CH3:11])[CH3:10]>>[C:9]([N:13]1[C:17](=[O:18])[C:16]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:2][C:3]3[CH:7]=[C:6]([CH3:8])[O:5][N:4]=3)[CH2:22][CH2:21]2)=[C:15]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[S:14]1(=[O:33])=[O:32])([CH3:12])([CH3:10])[CH3:11]

Participants

Reactant 2

HCID 27763043-(Bromomethyl)-5-methylisoxazole

HCID 67241221HCID 67241221, compound

Product 1

HCID 67241878HCID 67241878, compoundYield 17%

Procedure

The title compound was prepared as described for Example 104 from 3-(bromomethyl)-5-methylisooxazole and 2-tert-butyl-5-phenyl-4-(piperidin-4-ylamino)isothiazol-3(2H)-one 1,1-dioxide (Example 75) to give the title compound (0.021 g, 17%) as a solid. 1H NMR (500 MHz CDCl3): δ 7.52-7.48 (m, 2H), 7.48-7.42 (m, 3H), 5.92 (s, 1H), 5.18 (d, 1H), 3.40 (s, 2H), 2.98-2.88 (m, 1H), 2.70-2.62 (m, 2H), 2.40 (s, 3H), 1.74 (m, 9H), 1.79-1.60 (m, 4H), 1.42-1.32 (m, 2H); 13C NMR (125 MHz CDCl3): δ 169.7, 161.7, 159.9, 134.2, 131.8, 130.1, 128.9, 125.3, 106.9, 101.8, 61.8, 53.4, 52.0, 50.1, 32.5, 27.8, 12.5; Mass Spectrum M+H+ 459.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-ff2f42d3674946d78d999fe7bb4941de
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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