Ethylamine → methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylate

HRID 1875011Notes

Reaction equation

HRID 1875011 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].[CH3:14][CH2:15][N:16](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)C>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:11]([NH:16][CH2:15][CH3:14])=[O:13])=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 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 68488034methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylateYield 41.2%

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 (0.193 ml, 1.105 mmol), HATU (0.168 g, 0.442 mmol), and ethyl amine (0.045 g, 0.553 mmol) and the reaction stirred at RT for 2 h. Purification was accomplished by HPLC to afford methyl 3-chloro-4-[(ethylamino)carbonyl]-1H-pyrrole-2-carboxylate (0.035 g, 41% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s., 1H) 7.81 (t, 1H) 7.48 (d, 1H) 3.80 (s, 3H) 3.20 (dd, 2H) 1.08 (t, 3H). MS: m/z 231.0 (M+1).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-a3f2c04ec8b849c89c85bd5586e02ff2
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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