Benzyl {[3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]amino}sulfonylcarbamate → N-[3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]sulfamide

HRID 494484Notes

Reaction equation

HRID 494484 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:44][CH2:45][CH3:46])([CH2:41][CH2:42][CH3:43])[C:7](=[O:40])[C:8]([C:13]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([NH:23][S:24]([NH:27]C(=O)OCC5C=CC=CC=5)(=[O:26])=[O:25])=[CH:22][C:16]=4[S:15](=[O:39])(=[O:38])[N:14]=3)=[C:9]2[OH:12])=[CH:4][CH:3]=1>[Pd].CO.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:44][CH2:45][CH3:46])([CH2:41][CH2:42][CH3:43])[C:7](=[O:40])[C:8]([C:13]3[NH:18][C:17]4[CH:19]=[CH:20][C:21]([NH:23][S:24]([NH2:27])(=[O:25])=[O:26])=[CH:22][C:16]=4[S:15](=[O:39])(=[O:38])[N:14]=3)=[C:9]2[OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 136375602Benzyl {[3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]amino}sulfonylcarbamate

Product 1

HCID 136337523N-[3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]sulfamideYield 57.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of the product of Example 17D (28 mg, 0.042 mmol) in 2:1 methanol-ethyl acetate (15 mL) was treated with 10% Pd/C (20 mg) and hydrogenated at one atmosphere for 18 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound (13 mg).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-1d8099be827b44928886cf91333d1bc0
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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