Diisopropylethylamine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid pyrrolidin-1-yl-amide

HRID 1920904Notes

Reaction equation

HRID 1920904 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([C:20]([OH:22])=O)[O:17][N:16]=1.F[B-](F)(F)F.[N:28]1(OC(N(C)C)=[N+](C)C)[C:32]2[CH:33]=[CH:34][CH:35]=CC=2N=[N:29]1.C(N(CC)C(C)C)(C)C.Cl.NN1CCCC1>CN(C=O)C>[N:28]1([NH:29][C:20]([C:18]2[O:17][N:16]=[C:15]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])[CH:19]=2)=[O:22])[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 674920693-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid

Product 1

HCID 468969843-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid pyrrolidin-1-yl-amideYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (120 mg, 0.4 mmol) in DMF (5 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (192 mg, 0.6 mmol), N,N-diisopropyl ethyl amine (340 μL, 2.0 mmol) and N-aminopyrrolidine HCl (64 mg, 0.52 mmol). The resulting reaction mixture was for 4 h at room temperature. Concentration and purification by chromatography (silica, dichloromethane:methanol=1:0 to 4:1) afforded the title compound (108 mg, 73%) as a colourless oil. MS: m/e=369.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=1:0 to 4:1)

Sources & evidence

ORD record
ord-3983f161880d4d9a85810fd66e00ba27
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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