1,3-Dibromo-5,5-dimethylhydantoin → N-[3-(5-bromo-4-hydroxy-1-isopentyl-2-oxo-1,2-dihydro-3-pyridinyl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]methanesulfonamide

HRID 601435Notes

Reaction equation

HRID 601435 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:4](=[O:13])[C:3]=1[C:14]1[NH:19][C:18]2[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:17]=2[S:16](=[O:30])(=[O:29])[N:15]=1.[Br:31]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[Br:31][C:7]1[C:2]([OH:1])=[C:3]([C:14]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:17]=3[S:16](=[O:30])(=[O:29])[N:15]=2)[C:4](=[O:13])[N:5]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:6]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 136036674N-[3-(4-hydroxy-1-isopentyl-2-oxo-3-pyridyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

Product 1

HCID 136036672N-[3-(5-bromo-4-hydroxy-1-isopentyl-2-oxo-1,2-dihydro-3-pyridinyl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]methanesulfonamideYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 470A (0.258 g, 0.57 mmol) in tetrahydrofuran (10 mL) was treated with 1,3-dibromo-5,5-dimethyl hydantoin (0.24 g, 0.84 mmol) at 25° C. for 18 hours. The solvent was under a warm stream of nitrogen and the residue was chromatographed on silica gel eluting with dichloromethane to provide the title compound (0.13 g, 43%). 1H NMR (300 MHz, DMSO-d6) δ 0.94 (d, J=6.25 Hz, 6 H) 1.61 (m, 3 H) 3.08 (s, 3 H) 4.00 (m, 2 H) 7.56 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=2.21 Hz, 1 H) 7.70 (m, 1 H) 8.59 (s, 1 H) 10.26 (s, 1 H) 14.29 (s, 1 H). MS (ESI−) m/z 532 (M−H)−.

Workup

  1. customthe residue was chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-ee5d4edd37b34955a6fbd7b56d531a21
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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