Cesium carbonate → 2-[[3-(4,4-dibutyl-1-hydroxy-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]oxy]acetamide

HRID 494458Notes

Reaction equation

HRID 494458 reaction equation
[CH2:1]([C:5]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:19]=3[S:18](=[O:28])(=[O:27])[N:17]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].Br[CH2:35][C:36]([NH2:38])=[O:37].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:5]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([O:26][CH2:35][C:36]([NH2:38])=[O:37])=[CH:25][C:19]=3[S:18](=[O:28])(=[O:27])[N:17]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 696322-BromoacetamideHCID 1363755991,1-dibutyl-4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-2(1H)-naphthalenone

Product 1

HCID 1354401942-[[3-(4,4-dibutyl-1-hydroxy-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]oxy]acetamideYield 76%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 5E (69 mg, 0.15 mmol), 2-bromoacetamide (80 mg, 0.58 mmol), cesium carbonate (96 mg, 0.58 mmol), and tetrabutylammonium iodide (26 mg, 0.08 mmol) in N,N-dimethylformamide (2.4 mL) was stirred at 25° C. for 48 hours, diluted with ethyl acetate and treated with saturated ammonium chloride solution (2 mL). The organic layer was washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (58 mg, 76%). 1H NMR (300 MHz, DMSO-d6): δ 13.73 (s, 1 H), 8.17 (d, J=7.72 Hz, 1 H), 7.74 (m, 3 H), 7.55 (m, 1 H), 7.40 (m, 2 H), 4.59 (s, 2 H), 2.19 (m, 2 H), 2.02 (d, 2 H), 1-06 (m, 4 H), 0.90 (m, 2H), 0.69 (q, J=7.60 Hz, 6 H), 0.52 (m, 2 H).

Workup

  1. washThe organic layer was washed with water (3×) and saturated sodium chloride solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd8534b3f0f74a66a4acefc8cc4b8d77
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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