Triethylamine → HCID 86627482, compound

HRID 1969956Notes

Reaction equation

HRID 1969956 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].[CH2:22]([N:24](CC)[CH2:25]C)C.Cl.CNC>>[CH3:22][N:24]([CH3:25])[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[CH:18][C:8]=3[C:7]=2[CH:6]=1)(=[O:3])=[O:4].[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627482HCID 86627482, compoundYield 47%

Procedure

This compound is prepared according to synthesis 25, from 115 mg (0.35 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 2), 147 μL (1.05 mmol) of triethylamine and 35 mg (0.42 mmol) of dimethylamine hydrochloride. After purification by chromatography on silica (eluent dichloromethane/methanol 95/5) then trituration in methanol, 30 mg (24%) of 8-dimethylsulfamoyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-ccb895e8bd784109a8a588fe2f1696a2
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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