2,6-Lutidine → HCID 178468691, compound

HRID 247863Notes

Reaction equation

HRID 247863 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([C:12](=[N:23]OC(=O)C)[CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=1)[CH3:2].N1C(C)=CC=CC=1C>C1(C)C=CC=C(C)C=1>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][C:12]1[C:7]2[C:8](=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:28])[CH:6]=2)[NH:11][N:23]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 54162109HCID 54162109, compound

Product 1

HCID 178468691HCID 178468691, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A solution of ethyl-4-amino-3-[3'-(N-tert-butyloxycarbonylamino)-1'-acetoxyiminopropyl]benzoate (2.8 g, 7.1 mmol) and 2,6-lutidine (0.83 ml, 7.1 mmol) in m-xylene (200 ml), was heated at reflux in Dean-Stark apparatus for 5 hours. The solution was then cooled to ambient temperature and the solvent evaporated in vacuo. The crude residue was purified by flash chromatography (eluent 1:1 petrol:ethyl acetate) to give the indazole (0.95 g, 67%) as a colourless oil. NMR (250 MHz, CDCl3) δ 1.42 (12H, m), 3.20 (2H, t, J=7 Hz), 3.65 (2H, m), 4.41 (2H, q, J=7 Hz), 5.09 (1H, br t), 7.44 (1H, d, J=9 Hz), 8.05 (1H, dd, J=9 and 2 Hz), 8.45 (1H, br s), 10.50 (1H, br s).

Workup

  1. temperatureat reflux in Dean-Stark apparatus for 5 hours
  2. customthe solvent evaporated in vacuo
  3. customThe crude residue was purified by flash chromatography (eluent 1:1 petrol:ethyl acetate)

Sources & evidence

ORD record
ord-30a4daa65bb64bea8b89df97667696a3
Source dataset
uspto-grants-1993_05
Patent number
US05208248

Reaction notes

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