Reaktion #2354762

ord-2c3185ee004846bdada63f62e9864932

Reaktionsgleichung

NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)c[nH]c12
5-(phenyl)-3-(4-piperidinyl)-1H-indole-7-carboxamide
O=S(=O)(Cl)c1ccc(CNCc2ccccc2)s1
5-{[(phenylmethyl)amino]methyl}-2-thiophenesulfonyl chloride
CCN(CC)CC
triethylamine
CCN(CC)CC
TEA
→
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)c4ccc(CNCc5ccccc5)s4)CC3)c[nH]c12
desired product
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)c4ccc(CNCc5ccccc5)s4)CC3)c[nH]c12
5-phenyl-3-{1-[(5-{[(phenylmethyl)amino]methyl}-2-thienyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide

Edukte

NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)c[nH]c12
5-(phenyl)-3-(4-piperidinyl)-1H-indole-7-carboxamide
O=S(=O)(Cl)c1ccc(CNCc2ccccc2)s1
5-{[(phenylmethyl)amino]methyl}-2-thiophenesulfonyl chloride
CCN(CC)CC
triethylamine
CCN(CC)CC
TEA

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewere reacted

Vorschrift

Following the general procedure in example 267, 5-(phenyl)-3-(4-piperidinyl)-1H-indole-7-carboxamide (32 mg, 0.1 mmol), 5-{[(phenylmethyl)amino]methyl}-2-thiophenesulfonyl chloride (45.3 mg, 0.15 mmol) and triethylamine (0.06 mL, 0.3 mmol) were reacted to form the desired product which was purified by Gilson HPLC (CH3CN/Water, 0.1% TFA) (20 mg, 34%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07858796B2uspto-grants-2010_12