HCID 22037743, compound → HCID 178470875, compound

HRID 23996Notes

Reaction equation

HRID 23996 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH2:26])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].Cl.[N:29]1([C:34]([NH2:36])=O)C=CC=N1>CO>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH:26][C:34]([NH2:36])=[NH:29])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 22037743HCID 22037743, compoundHCID 66819270HCID 66819270, compound

Product 1

HCID 178470875HCID 178470875, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[5-(2-aminooxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester (0.28 g, 0.75 mmol) and 1H-pyrazole-1-carboxamide hydrochloride (0.99 g, 0.67 mmol) were dissolved in methanol (3 mL) and stirred for 5 days. The solvent was evaporated under vacuum and the crude mixture was purified via column chromatography with silica gel, eluting with 10% methanol/dichloromethane to afford the title compound (97% yield). 1H NMR (CDCl3), δ 7.11-7.26 (m, 7H), 7.00 (d, 1H, J=2.3 Hz), 6.75 (dd, 1H, J=2.3, 8.8 Hz), 6.43 (d, 1H, J=3.2 Hz), 5.98 (t, 1H, J=7.6 Hz), 4.08 (m, 2H), 3.99 (m, 4H), 3.23 (m, 2H), 1.05 (t, 3H, J=7.2 Hz).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe crude mixture was purified via column chromatography with silica gel
  3. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-eb075bb8beba4a63bf11885de0bdc7ec
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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