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

HRID 1033

反応式

HRID 1033 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a5ca07eaa4874ceb97ba416d73a61749
出典データセット
uspto-grants-1998_03
特許番号
US05723477

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