Fumaric Acid → 5-(2-Furanyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

HRID 1489396

Reaction equation

HRID 1489396 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[CH:9]=[N:10][CH:11]=1.[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22]>CO>[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 196942835-(Furanyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

Product 1

HCID 196943225-(2-Furanyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarateYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-described pyridine derivative was converted to invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followed by recrystallization from ethyl acetate afforded 5-(2-furanyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (43%). M.p. 147°-148° C. (EtOAc); 1H NMR (DMSO-d6, 300 MHz): δ 8.71 (s, 1 H), 8.29 (s, 1 H), 7.93 (bs, 1 H), 7.64(s, 1 H), 6.95 (d, J=3 Hz, 1 H), 6.46 (bm, 1 H), 6.42 (s, 3 H), 3.40 (m, 1 H), 3.20 (m, 1 H), 2.39 (m, 1 H), 2.08 (m, 4 H), 1.74 (m, 3 H).

Workup

  1. customAfter 30 minutes the solvent was removed in vacuo
  2. customTrituration with diethyl ether followed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-39d182cd158b4605905953e591ec92b9
Source dataset
uspto-grants-1997_10
Patent number
US05677459

Linked notes

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