Methanesulfonic Acid → Rasagiline mesylate

HRID 505970노트

반응식

HRID 505970 반응식
[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1.[CH3:14][S:15]([OH:18])(=[O:17])=[O:16]>C(#N)C>[CH3:14][S:15]([OH:18])(=[O:17])=[O:16].[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1

참가 물질

4

반응물 2

HCID 6395Methanesulfonic AcidHCID 3052776Rasagiline

생성물 1

HCID 3052775Rasagiline mesylate수율 86.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
77.5 °C

실험 절차

The toluenic phase of step (a) was charged into a 500 mL round-bottomed flask under nitrogen and equipped with mechanical stirring. 110 mL of acetonitrile were then added, followed by the dropwise addition of 32.54 g of methanesulfonic acid in about 20 minutes, maintaining the temperature below 40° C. Precipitation started after the addition of approximately 10% of the total amount of methanesulfonic acid. The thick suspension thus obtained was heated up to 75-80° C. and stirred for 30 min. The suspension was then cooled down to 10-15° C., stirred for at least 1 hour and filtered. The collected solid was washed with 3×20 mL of acetonitrile to yield 74.27 g of yellowish wet product (70.95 g of dry crude, partial yield: 86.20%; 99.32% by HPLC).

후처리

  1. customequipped with mechanical stirring
  2. temperaturemaintaining the temperature below 40° C
  3. customPrecipitation
  4. additionafter the addition of approximately 10% of the total amount of methanesulfonic acid
  5. customThe thick suspension thus obtained
  6. temperatureThe suspension was then cooled down to 10-15° C.
  7. stirringstirred for at least 1 hour
  8. filtrationfiltered
  9. washThe collected solid was washed with 3×20 mL of acetonitrile

출처 및 근거

ORD 기록
ord-3f32644a789e4444b315d2286f624785
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781616B2

반응 노트

불러오는 중…