Ethanolamine → Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

HRID 1874964Notes

Reaction equation

HRID 1874964 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[Cl:5][C:6]1[CH:10]=[C:9]([C:11]([NH:4][CH2:3][CH2:1][OH:2])=[O:12])[NH:8][C:7]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 68487232Methyl 3-chloro-5-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylateYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethanolamine (0.175 mL, 2.90 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.150 g, 0.580 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. Purification was accomplished by silica gel column chromatography (30-100% EtOAc/hexanes) to afford the title compound (0.082 g, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.37 (br. s., 1H), 8.42 (t, 1H), 6.80 (s, 1H), 4.75 (t, 1H), 3.78 (s, 3H), 3.46 (q, 2H), 3.27 (q, 2H). LCMS: m/z 245.4 (M−1).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-20e73671c981424ea5001ff02cbebfd3
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…