Potassium Carbonate → 3-[1-({3-[(methyloxy)amino]propyl}sulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide

HRID 2267572Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].Cl.[CH3:33][O:34][NH2:35].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[I-].[Na+]>[CH3:33][O:34][NH:35][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (40.0 mg, 0.087 mmol) in DMSO (2.0 mL), were added O-methylhydroxylamine hydrochloride (83.5 mg, 1.0 mmol), K2CO3 (35.0 mg, 0.35 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°/o 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°/o TFA 10-90%)

Sources & evidence

ORD record: ord-b1037e570264453e881bd58c0147cfca
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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