Benzenesulfonyl chloride → HCID 86627488, compound

HRID 1969964Notes

Reaction equation

C(N(CC)CC)C.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:18][C:19]1[CH:28]=[CH:27][C:26]2[NH:25][C:24](=[O:29])[C:23]3[NH:30][CH:31]=[CH:32][C:22]=3[C:21]=2[CH:20]=1.[CH2:33]([C:35]([O-:37])=[O:36])[CH3:34]>CN(C)C=O>[C:8]1([S:14]([NH:18][C:19]2[CH:28]=[CH:27][C:26]3[NH:25][C:24](=[O:29])[C:23]4[NH:30][CH:31]=[CH:32][C:22]=4[C:21]=3[CH:20]=2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:33]([C:35]([O-:37])=[O:36])[CH3:34]

Participants

Conditions

Temperature: 40 °C

Procedure

62 μL (0.44 mmol) of triethylamine and then 31 μL (0.24 mmol) of benzenesulfonyl chloride are added to 60 mg (0.22 mmol) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 64) suspended in anhydrous dimethylformamide (1 mL). The solution is stirred for 1 h at 40° C. The solvent is evaporated and the raw product obtained is purified by recrystallization from methanol to give 51 mg (57%) of 8-benzenesulfonylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

customThe solvent is evaporated
customthe raw product obtained
customis purified by recrystallization from methanol

Sources & evidence

ORD record: ord-b6d05c2f40e045a4a84ee4ae73b74247
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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