3-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indole

HCID 54075398

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Basic information

CAS: 180637-89-2
Standard SMILES: CN1CCC[C@@H]1Cc1c[nH]c2ccc(C=CS(=O)(=O)c3ccccc3)cc12
InChIKey: MJICWWOZPCLNBP-LJQANCHMSA-N
Molecular formula: C22H24N2O2S
Average molar mass: 380.5 g/mol
Monoisotopic mass: 380.15584919

Names & identifiers

Preferred name: 3-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indole
IUPAC: 5-[2-(benzenesulfonyl)ethenyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole
English name: 3-[((2R)-1-Methylpyrrolidin-2-yl)methyl]-5-[(E)-2-(phenylsulfonyl)vinyl]indole
Molecular formula: C22H24N2O2S
Molecular weight: 380.5

Names & synonyms

3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethenyl]-1H-indoleRefChem:4879153-(((2R)-1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethenyl)-1H-indole180637-89-2(R)-3-((1-Methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)vinyl)-1H-indoleSCHEMBL505789DTXSID60939362(R)-5-(2-benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indoleMJICWWOZPCLNBP-LJQANCHMSA-NDB-353589(R)-5-(2-benzenesulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(R)-5-(2-benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1 H-indole

Show more names

Eletriptan Impurity 23(R)-3-(1-methyl-2-pyrrolidinylmethyl)-5-[2-phenylsulphonyl)vinyl]-1H-indole(R)5-(2-Benzenesulfonyl-vinyl)-3-(1-methyl-pyrrolidin-2-ylmethyl)-1H-indole(R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole3-[((2R)-1-Methylpyrrolidin-2-yl)methyl]-5-[(E)-2-(phenylsulfonyl)vinyl]indole(R)-3-[(1-methylpyrrolidin-2-yl)methyl]-5-[2-(phenylsulfonyl)ethenyl]-1H-indole(R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethenyl]-1H-indole1H-Indole, 3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethenyl]-

(R)-5-(2-Phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(R)-5-(2-Phenylsulphonylethenyl)-3-(N-methylpyrrolid in-2-ylmethyl)-1H-indole(R)-5-(2-Phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole(R)-5-(2benzenesulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole3-{[(2R)-1-Methyl-2-pyrrolidinyl]methyl}-5-[2-(phenylsulfonyl)vinyl]-1H-indole5-[2-(Benzenesulfonyl)ethen-1-yl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole

Database identifiers

CAS: 180637-89-2
PubChem CID: 54075398
DTXSID: DTXSID60939362

Properties

Computed structural properties

XLogP: 4.1
Topological polar surface area: 61.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 27
Formal charge: 0
Complexity: 621

Physicochemical properties

Boiling point: 617.7 · 617.7±55.0 °C(Predicted)
Density: 1.263 · 1.263
solubility: soluble in Dichloromethane, Dimethylformamide, Methanol
pka: 16.92 · 16.92±0.30(Predicted)
FDA UNII: 571 D9TF · FEU571D9TF
Symbol(GHS): 5 · GHS05,GHS08,GHS07
Signal word: Danger
Hazard statements: 302 · H302-H317-H318-H373
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P280-P305+P351+P338-P310-P260-P314-P501
REACH Registrations: Inactive

Safety & regulation

Safety data

Signal word: Danger
Symbol(GHS): GHS05,GHS08,GHS07
Hazard statements: H302-H317-H318-H373
REACH Registrations: Inactive
Precautionary statements: P264-P270-P301+P312-P330-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P280-P305+P351+P338-P310-P260-P314-P501

Chemistry & industry

Applications · 1 item

Uses(R)-5-(2-Benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole is the free base of (R)-5-(2-Benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole Hydrobromide (B120725), which is an impurity of Eletriptan (E505000). Eletriptan is a selective serotonin 5-HT1B and 5-HT1D receptor agonist and used to treat migraines (1,2,3). (R)-5-(2-Benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole is also an intermediate in the synthesis of 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-1-[1-[3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-indol-5-yl]-2-(phenylsulfonyl)ethyl]-5-[(1E)-2-(phenylsulfonyl)ethenyl]-1H-indole (M320195).