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3-(((R)-1-methylpyrrolidin-2-yl)methyl)-1-(2-(phenylsulfonyl)ethyl)-5-((E)-2-(phenylsulfonyl)vinyl)-1H-indole

IP.com Disclosure Number: IPCOM000176131D
Publication Date: 2008-Nov-06
Document File: 2 page(s) / 75K

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3-(((R)-1-methylpyrrolidin-2-yl)methyl)-1,5-bis(2-(phenylsulfonyl)ethyl)-1H-indole

3-(((R)-1-methylpyrrolidin-2-yl)methyl)-1,5-bis(2-(phenylsulfonyl)ethyl)-1H-indole ("IMP5a") of the following formula

O

S O

is an impurity formed during the preparation of 5-(E) (R) 2-benzenesufonyl-vinyl)-3-(1- methyl-pyrrolidine-2-ylmethyl)-1H-indole), an intermediate in the preparation of

3-[[(R]-1-methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]indole ("ELT"), of the following formula

N

 ELT is used for the acute treatment of migraine with or without aura in adults. It is a selective 5-hydroxytryptamine 1B/1D receptor agonist, which is administrated as the hydrobromide salt of ELT (ELT-HBr).

ELT tablets are marketed by Pfizer under the name RELPAX®.

The obtained isolated IMP6 was analyzed by NMR and the spectrum described herein below:

1H NMR DATA:

(400 MHz, CDCl3) δ 1.211-1.252 (m,2H), 1.377 (s,2H),1.738-1.823 (m,2H),2.248-

2.315 (m,2H),2.416 (s,3H),2.522 - 2.578 (m,2H),3.062-3.105 (m,2H),3.33-3.37

(m,2H),3.435-3.472 (m,2H),4.44-4.476 (m,2H),6.480 (s,1H),6.876-6.901

(d,1H),7.011-7.032 (d,1H),7.213-7.231 (d,1H),7.457-7.654 (m,6H),7.787-7.809

(d,2H),7.906-7.928 (d,2H)

13CNMR:

(CDCl3)δ21.81,26.91,29.05,31.0,39.65,40.73,55.44,57.39,58.31,66.81,109.23,118.77,

122.55,126.15,127.74,128.52,128.74,129.38,129.44,133.82,134.10,134.73,138.71,139

.03

N

N

O

S

O

O O

S

N

H

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Example

-

3

:

(((

)

R

-

-

methylpyrrolidin

-

1

-

2

)

yl

m...