Triethylamine → HCID 86627520, compound

HRID 1970004Notes

Reaction equation

HRID 1970004 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].[NH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1.C(N(CC)CC)C>>[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[CH:23]([NH:22][S:2]([C:5]1[CH:14]=[CH:13][C:12]3[NH:11][C:10](=[O:15])[C:9]4[NH:16][CH:17]=[CH:18][C:8]=4[C:7]=3[CH:6]=1)(=[O:3])=[O:4])[CH2:24]2.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 1232383-AminoquinuclidineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627520HCID 86627520, compoundYield 8.2%

Procedure

This compound is prepared according to synthesis 25, from 200 mg (0.6 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 2), 100 mg (0.8 mmol) of 3-aminoquinuclidine (in free form) and 170 μL (1.22 mmol) of triethylamine. After purification by chromatography on silica (eluent chloroform/methanol/ammonia 85/13/2), 11 mg (4%) of 8-(1-azabicyclo[2.2.2]oct-3-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a brown solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent chloroform/methanol/ammonia 85/13/2)

Sources & evidence

ORD record
ord-9376e52fb4f246bba0117deedf2ee071
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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