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

HRID 1489397

반응식

HRID 1489397 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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, 2 H), 8.26 (s, 1 H), 6.25 (s, 3 H), 4.24 (bm, 1 H), 3.53 (bm, 1 H), 3.03 (bm, 1 H), 2.43 (s, 3 H), 2.27 (m, 1 H), 1.9-2.1 (m, 3 H), 0.0 (s, 9 H).

후처리

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

출처 및 근거

ORD 기록
ord-a72ce20af755469dab6266769c6cb7e2
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677459

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