Diethyl Sulfate → N-(8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)-4-oxo-3,5-dihydropyrrolo[2,3-c]quinoline-8-sulfonamide;propanoate

HRID 1970021Notes

Reaction equation

HRID 1970021 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:29]1[CH:34]2[CH2:35][CH2:36][CH:30]1[CH2:31][CH:32]([NH2:37])[CH2:33]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OS(OCC)(=O)=O)C>>[CH2:22]([N:29]1[CH:30]2[CH2:36][CH2:35][CH:34]1[CH2:33][CH:32]([NH:37][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])[CH2:31]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1.[CH2:18]([C:19]([O-:21])=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 6163Diethyl SulfateHCID 128321038-Benzyl-8-azabicyclo(3.2.1)octan-3-amineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 86627529N-(8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)-4-oxo-3,5-dihydropyrrolo[2,3-c]quinoline-8-sulfonamide;propanoate

Procedure

8-(8-Benzyl-8-aza-bicyclo[3.2.1]oct-3-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is prepared according to synthesis 111, from 360 mg (1.1 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid and 238 mg (1.1 mmol) of 8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylamine to give, after esterification according to general method C (using diethylsulfate as the dialkylsulfate) and precipitation in water, 411 mg (69% in two stages) of 8-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a brown solid.

Workup

  1. customto give
  2. customprecipitation in water

Sources & evidence

ORD record
ord-7a2062d912e6491dba17e3a528902a70
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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