Sodium Carbonate → N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

HRID 1988926Notes

Reaction equation

HRID 1988926 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[CH2:3]C1.Br[C:24]1[CH:39]=[CH:38][C:27]2[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=2[CH:25]=1.[C:40](=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:4]1([NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][C:10]([CH3:40])=[C:9]([C:24]3[CH:39]=[CH:38][C:27]4[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=4[CH:25]=3)[CH:8]=2)[CH2:1][CH2:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 586564962-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide2×HCID 68676775HCID 68676775, compound2×

Product 1

HCID 10453183N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.04 g) 2-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide (Intermediate 35) (0.04 g) 2M aqueous sodium carbonate (1.5 ml) and tetrakis(triphenylphosphine)palladium(0) (1 mg) in isopropanol (3 ml) was stirred at reflux under nitrogen for 18 h. The mixture was absorbed onto silica (Merck 7734) and applied to a Varian Bond-Elut SPE cartridge (silica, 5 g) and eluted with a toluene:ethanol gradient (100:0 to 0:100) to give the title compound as a white solid (0.03 g).

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. customThe mixture was absorbed onto silica (Merck 7734)
  3. washeluted with a toluene

Sources & evidence

ORD record
ord-f8dd1ace81eb419484916977c6880292
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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