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

HRID 724898

反応式

HRID 724898 の反応式
[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH3:14])[CH:6]=[N:7][CH:8]=1.[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>CO>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[CH3:1][Si:2]([CH3:15])([CH3:16])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH3:14])[CH:6]=[N:7][CH:8]=1

参加物

4

反応物 2

HCID 444972Fumaric AcidHCID 196942965-(Trimethylsilyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

生成物 1

HCID 196943035-Trimethylsilyl-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate収率 51%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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 (5 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-trimethylsilyl-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (51%). M.p. 161°-162° C. (EtOAc); 1H NMR (D2O, 300 MHz): δ 8.48 (s, 2H), 8.26 (s, 1H), 6.25 (s, 3H), 4.24 (bm, 1H), 3.53 (bm, 1H), 3.03 (bm, 1H), 2.43 (s, 3H), 2.27 (m, 1H), 1.9-2.1 (m, 3H), 0.0 (s, 9H).

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-aeb9debf4b084fd1a132e4a0e56102e0
出典データセット
uspto-grants-1998_01
特許番号
US05705512

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