Methyl 3-(bromomethyl)benzoate → HCID 11642012, compound

HRID 2422108Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:13]([N:17]1[C:21](=[O:22])[C:20]([NH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[C:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:18]1(=[O:37])=[O:36])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([N:17]1[C:21](=[O:22])[C:20]([NH:23][CH:24]2[CH2:29][CH2:28][N:27]([CH2:2][C:3]3[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=3)[C:6]([O:8][CH3:9])=[O:7])[CH2:26][CH2:25]2)=[C:19]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:18]1(=[O:37])=[O:36])([CH3:16])([CH3:14])[CH3:15]

Participants

Reactant 2

HCID 517981Methyl 3-(bromomethyl)benzoate

HCID 67241221HCID 67241221, compound

Product 1

HCID 11642012HCID 11642012, compoundYield 48%

Procedure

The title compound was prepared as described for Example 104 from methyl 3-(bromomethyl)benzoate and 2-tert-butyl-5-phenyl-4-(piperidin-4-ylamino)isothiazol-3(2H)-one 1,1-dioxide (Example 75) to give the title compound (0.101 g, 48%) as a solid. 1H NMR (500 MHz CDCl3): δ 7.95-7.87 (m, 2H), 7.54-7.32 (m, 7H), 5.20 (d, 1H), 3.92 (s, 3H), 3.38 (s, 2H), 3.00-2.80 (m, 1H), 2.66-2.58 (m, 2H), 1.80-1.54 (m, 13H), 1.42-1.30 (m, 2H); 13C NMR (125 MHz CDCl3): δ 167.4, 159.9, 139.1, 134.3, 133.6, 131.8, 130.4, 130.2, 129.9, 128.8, 128.6, 125.4, 106.8, 62.5, 61.8, 52.3, 51.9, 50.2, 32.5, 27.8; Mass Spectrum: M+H+ 512.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-103e36bc2ed8403494c8cc9bd0fe1342
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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