Ethanolamine → methyl 3-chloro-4-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate

HRID 1875013Notes

Reaction equation

HRID 1875013 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([OH:13])=O)=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:47]([CH2:49][NH2:50])[OH:48]>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:11]([NH:50][CH2:49][CH2:47][OH:48])=[O:13])=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684862114-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid

Product 1

HCID 68487062methyl 3-chloro-4-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylateYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid (0.075 g, 0.368 mmol) in DMF (1 ml) was added DIPEA (0.097 ml, 0.553 mmol), HATU (0.168 g, 0.442 mmol) and ethanolamine (0.033 ml, 0.553 mmol) and the reaction stirred at RT for 3 h. Purification was accomplished by HPLC to afford methyl 3-chloro-4-{[(2-hydroxyethyl)amino]carbonyl}-1H-pyrrole-2-carboxylate (0.06 g, 53% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s., 1H) 7.78 (t, 1H) 7.52 (d, 1H) 4.28 (br. s., 1H) 3.80 (s, 3H) 3.56-3.68 (m, 1H) 3.46 (t, 1H) 3.25 (q, 1H) 3.07-3.21 (m, 1H). MS: m/z 247.0 (M+1).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-79a0af88ac6a4e66a19ccf47659433cf
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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