Fumaric Acid → 5-(4-Fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

HRID 1941265

反応式

HRID 1941265 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:19])[CH:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>CO>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH3:19])[CH:11]=[N:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 444972Fumaric AcidHCID 196943055-(4-Fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

生成物 1

HCID 196943045-(4-Fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate収率 63%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The pyridine derivative described above was converted to a compound of the invention having 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-(4-fluorophenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (63%). M.p. 159°-160° C. (EtOAc); 1H NMR (D2O, 300 MHz): δ8.87 (s, 1H), 8.68 (s, 1H), 8.26 (s, 1H), 7.73 (dd, J=8, 6 Hz, 2H), 7.30 (app. t, J=8 Hz, 2H), 6.61 (s, 2H), 4.56 (bm, 1H), 3.91 (bm, 1H), 3.41 (bm, 1H), 2.83 (s, 3H), 2.67 (m, 1H), 2.3-2.5 (m, 3H).

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-9885573922aa41b0ba00a610a04ebf31
出典データセット
uspto-grants-1997_12
特許番号
US05703100

関連ノート

読み込み中…