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

HRID 1875009Notes

Reaction equation

HRID 1875009 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][N:15](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:16].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CNC>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:11]([N:15]([CH3:16])[CH3:14])=[O:13])=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 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 68487372methyl 3-chloro-4-[(dimethylamino)carbonyl]-1H-pyrrole-2-carboxylateYield 49.5%

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 HATU (0.168 g, 0.442 mmol), DIPEA (0.097 ml, 0.553 mmol) and dimethyl amine (2M in THF) (0.276 ml, 0.553 mmol) and the reaction stirred at RT for 1 h. Purification was accomplished by HPLC to afford methyl 3-chloro-4-[(dimethylamino)carbonyl]-1H-pyrrole-2-carboxylate (0.042 g, 49% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.40 (br. s., 1H) 7.23 (d, 1H) 3.80 (s, 3H) 2.93 (s, 6H). MS: m/z 231.0 (M+1).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-acc59fe774714ce780319e1c84443d50
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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