Sodium Carbonate → N-Cyclopropyl-3-[3-({[2-hydroxy-1-(hydroxymethyl)ethyl]amino}methyl)-1,2-benzisoxazol-6-yl]-4-methylbenzamide

HRID 1988918Notes

Reaction equation

HRID 1988918 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]2[C:6]([CH2:9][NH:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[N:7][O:8][C:4]=2[CH:3]=1.[CH:18]1([CH2:21][NH:22][C:23](=[O:39])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:20]C1.[C:40](=O)([O-])[O-].[Na+].[Na+]>CC(O)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:21]1([NH:22][C:23](=[O:39])[C:24]2[CH:25]=[CH:26][C:27]([CH3:40])=[C:28]([C:2]3[CH:17]=[CH:16][C:5]4[C:6]([CH2:9][NH:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[N:7][O:8][C:4]=4[CH:3]=3)[CH:29]=2)[CH2:18][CH2:20]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 586564522-[(6-Bromo-1,2-benzisoxazol-3-yl)methyl]amino-1,3-propanediol2×HCID 68676775HCID 68676775, compound2×

Product 1

HCID 58656515N-Cyclopropyl-3-[3-({[2-hydroxy-1-(hydroxymethyl)ethyl]amino}methyl)-1,2-benzisoxazol-6-yl]-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 2-[(6-bromo-1,2-benzisoxazol-3-yl)methyl]amino-1,3-propanediol (Intermediate 2, 8 mg), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 5, 10 mg) aqueous sodium carbonate (1M, 0.1 ml) and tetrakis(triphenylphosphine)palladium(0) (1 mg) in 2-propanol (0.2 ml) was stirred at 80° under nitrogen for 18 h. The solvent was evaporated and the residue was purified on a Varian Bond-Elut SPE cartridge (silica, 500 mg) using a dichloromethane-methanol elution gradient (19:1 to 9:1) to give the title compound as an oil (3 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a Varian Bond-Elut SPE cartridge (silica, 500 mg)
  3. washa dichloromethane-methanol elution gradient (19:1 to 9:1)

Sources & evidence

ORD record
ord-4cfa7c39ba4f4f13a847f48d6d3bd6b5
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…