Pyridine → tert-Butyl [5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamate

HRID 1772894Notes

Reaction equation

HRID 1772894 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-])=O.[C:14]([O:18][C:19](=[O:31])[NH:20][CH2:21][C:22]1[C:23]([O:29][CH3:30])=[N:24][CH:25]=[C:26]([NH2:28])[CH:27]=1)([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].C(N(CC)CC)C>O1CCOCC1.O.CCO.CN(C=O)C.[Pd]>[C:14]([O:18][C:19](=[O:31])[NH:20][CH2:21][C:22]1[C:23]([O:29][CH3:30])=[N:24][CH:25]=[C:26]([N:28]2[C:38](=[O:39])[NH:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:10]2(=[O:12])=[O:11])[CH:27]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

10

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 131734691Tert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamate

Product 1

HCID 131734693tert-Butyl [5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamateYield 96.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolventHCID 19096565Water ethanolSolvent

Procedure

The title compound (2.12 g, 4.84 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (1.11 g, 5.0 mmol), tert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamate (IntA34) (1.39 g, 5.5 mmol) and pyridine (1.21 mL, 15.0 mmol) in 1,4-dioxane (20 mL); followed by followed by 10% Pd/C (212 mg) in water/EtOH (1:1, 100 mL); followed by 1,1′-carbonyldiimidazole (1.14 g, 7.02 mmol) and triethylamine (0.49 mL, 3.51 mmol) in DMF (8 mL) using the methods of (IntA1), step 1 and (IntA14), steps 2 and 3.

Sources & evidence

ORD record
ord-459c0a9b210f48d89189f209fbd693ed
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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