Triethylamine → HCID 86627485, compound

HRID 1969959Notes

Reaction equation

HRID 1969959 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(CC)CC)C.Cl.[NH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]>>[CH2:36]([O:35][C:33]([CH2:32][CH2:31][NH:30][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])=[O:34])[CH3:22].[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627485HCID 86627485, compoundYield 32.7%

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 59 mg (0.42 mmol) of methyl 3-aminopropanoate hydrochloride. After purification by chromatography on silica (eluent dichloromethane/methanol 96/4), 25 mg (18%) of 8-(2-ethoxycarbonyl-ethylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a gray solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent dichloromethane/methanol 96/4)

Sources & evidence

ORD record
ord-646b32a710dd4d1983b4f6b8b902b7f9
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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