Dimethylamine → HCID 54017257, compound

HRID 1527186Notes

Reaction equation

HRID 1527186 reaction equation
COC([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=2)[CH:7]=[CH:6]1)=O.CNC>CCO>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH:7]=[CH:6][NH:5]2)=[CH:9][CH:10]=1)[CH3:19]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 68284299HCID 68284299, compound

Product 1

HCID 54017257HCID 54017257, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-ethoxycarbonylmethyl-indole-1-carboxylic acid methyl ester (965 mg, 3.25 mmol) in EtOH (10 mL) was added dimethylamine (˜5.6 M in EtOH, 24.4 mL, 48.8 mmol) and the solution was stirred at RT overnight. EtOH was concentrated and the crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 85:15) to give the desired material. MS (UPLC): 204.2 [M+H]+, 221.2 [M+NH4]+, 248.2 [M+HCOO]−; tR (HPLC conditions f): 1.87 min.

Workup

  1. concentrationEtOH was concentrated
  2. customthe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 85:15)

Sources & evidence

ORD record
ord-7d90f581d24d489e9d710ae9f9b4d11b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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