Potassium Carbonate → HCID 59003288, compound

HRID 2267571Notes

Reaction equation

[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].Cl.[CH3:31][O:32][NH2:33].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[I-].[Na+]>[CH3:31][O:32][NH:33][CH2:2][CH2:1][S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 3-[1-(ethenylsulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide (41 mg, 0.1 mmol) in DMSO (2.0 mL), were added O-methylhydroxylamine hydrochloride (83.5 mg, 1.0 mmol), K2CO3 (70.0 mg, 0.70 mmol) and sodium iodide (0.5 mg). The reaction solution was heated to 80° C. overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (20.7 mg, 43%).

Workup

concentrationThe reaction mixture was concentrated
custompurified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

Sources & evidence

ORD record: ord-ddd8c3723d0848f59e04d4d30ca0cde2
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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