4-Methylmorpholine → 2-(4-benzyloxy-phenyl)-N-{1-[2-(2-oxo-oxazolidin-3-yl)-ethyl]-1H-indazol-6-yl}-acetamide

HRID 1790154Notes

Reaction equation

HRID 1790154 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[CH:4][CH:3]=1.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](O)=[O:35])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[CH2:19]([O:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][C:34]([NH:1][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][O:15][C:14]3=[O:18])=[CH:4][CH:3]=2)=[O:35])=[CH:31][CH:32]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 220365653-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-oneHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 113518822-(4-benzyloxy-phenyl)-N-{1-[2-(2-oxo-oxazolidin-3-yl)-ethyl]-1H-indazol-6-yl}-acetamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-one (58 mg, 0.24 mmol), 4-benzyloxyphenylacetic acid (68 mg, 0.28 mmol), ethyldimethylpropylcarbodiimide hydrochloride (53 mg, 0.28 mmol), N-hydroxybenzotriazole (37 mg, 0.28 mmol) and N-methyl morpholine (60 mg, 0.56 mmol) in 3 mL of DMF was stirred at room temperature for 6 hours. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel, ethyl acetate/triethylamine, 30/1) to provide the title compound as a pale yellow solid (58 mg, 52%); 1H NMR (300 MHz, DMSO-d6) ppm 3.39 (m, 2H), 3.55 (m, 2H), 3.61 s, 2H0, 4.09 (m, 2H), 4.47 (m, 2H), 5.09 (s, 2H), 6.67 (d, J=8.47, 2H), 7.13 (m, 1H), 7.27 (m, 2H), 7.31–7.45 (m, 5H), 7.65 (m, 1H), 7.97 (m, 1H), 8.13 (s, 1H), 10.30 (s, 1H); MS (DCI/NH3) m/z 471 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/triethylamine, 30/1)

Sources & evidence

ORD record
ord-6a1b0502c1d14ea5b84ec72be69c1c58
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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