Triethylamine → 8-(Methyl-prop-2-ynyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

HRID 1970022Notes

Reaction equation

HRID 1970022 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].C(N(CC)CC)C.[CH3:29][NH:30][CH2:31][C:32]#[CH:33].C(OS(OCCC)(=O)=O)CC>>[CH3:29][N:30]([CH2:31][C:32]#[CH:33])[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])[CH2:8][CH3:7]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 69015Sulfuric acid, dipropyl esterHCID 96160N-methylpropyn-2-ylamineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 1317305238-(Methyl-prop-2-ynyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-propyl carboxylate

Procedure

This compound is prepared according to synthesis 111, from 196 mg (0.6 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid, 242 μL (2.4 mmol) of triethylamine and 45 mg (0.66 mmol) of N-methyl-prop-2-ynyl-amine to give, after esterification according to general method C (using di-n-propylsulfate as the dialkylsulfate) and purification by chromatography on silica (eluent dichloromethane/methanol 97/3) then trituration in diethyl ether, 80 mg (33% in two stages) of 8-(methyl-prop-2-ynyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customto give
  3. custompurification by chromatography on silica (eluent dichloromethane/methanol 97/3)

Sources & evidence

ORD record
ord-a5e41ddca5224196be09466d05b6650b
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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