Triethylamine → HCID 86627492, compound

HRID 1969967Notes

Reaction equation

C(N(CC)CC)C.[NH2:8][C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1.Cl.[CH2:24]([C:26]([OH:28])=[O:27])[CH3:25].[F:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>CN(C)C=O>[F:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:8][C:9]2[CH:18]=[CH:17][C:16]3[NH:15][C:14](=[O:19])[C:13]4[NH:20][CH:21]=[CH:22][C:12]=4[C:11]=3[CH:10]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1.[CH2:24]([C:26]([O-:28])=[O:27])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

82 μL (0.59 mmol) of triethylamine is added to 60 mg (0.20 mmol) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride (synthesis 64) suspended in anhydrous dimethylformamide (1 mL). The mixture is cooled to 0° C., then 42 mg (0.21 mmol) of 4-fluoro-benzenesulfonyl chloride is added. The solution is stirred for 1 h at 0° C. The solvent is evaporated and the raw product obtained is purified by recrystallization from methanol to give 32 mg (38%) of 8-(4-fluoro-benzenesulfonylamino)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a light brown solid.

Workup

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

Sources & evidence

ORD record: ord-9a157dc093f044debcf8ac1fab4280ef
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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