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

HRID 1489398

Reaction equation

HRID 1489398 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH3:20])[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>CO>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH3:20])[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 196943425-Phenylethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine

Product 1

HCID 196943415-(Phenylethynyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarateYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (10 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 isopropyl acetate afforded 5-(phenylethynyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (56%). M.p. 152°-154° C. (decorap., iPrOAc); 1H NMR (DMSO-d6, 300 MHz): δ 9.6-10.4 (bs, 1 H), 8.5-8.9 (bs, 1 H), 8.00 (s, 1 H), 7.60(m, 2 H), 7.46 (m, 3 H), 6.63 (s, 3 H), 3.51 (app. t, J=8 Hz, 1 H), 3.33 (app. t, J=8 Hz, 1 H), 2.51 (m, 1 H), 2.24 (s, 3 H), 2.19-2.32 (m, 1 H), 1.7-2.0 (m, 3 H).

Workup

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

Sources & evidence

ORD record
ord-e1e8fef28d3c4f8caf2ae42fee18700e
Source dataset
uspto-grants-1997_10
Patent number
US05677459

Linked notes

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