Methanesulfonic Acid → 3-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine

HRID 2200324노트

반응식

HRID 2200324 반응식
[Br:1][C:2]1[C:3]([CH3:13])=[N:4][C:5]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[CH:6][CH:7]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.CS(O)(=O)=O.C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[C:3]([CH3:13])=[N:4][C:5]([C:8]2[N:12]=[CH:11][N:10]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][O:14]3)[N:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 178432647HCID 178432647, 화합물

생성물 1

HCID 582983093-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
68 °C

실험 절차

3-Bromo-2-methyl-6-(4H-1,2,4-triazol-3-yl)pyridine (1 equiv), 3,4-dihydro-2H-pyran (2 equiv) and methanesulfonic acid (0.1 equiv) were combined in tetrahydrofuran. The reaction was heated to 68° C. for 3.5 h, cooled to room temperature, and treated with triethylamine (0.4 equiv). The reaction mixture was concentrated under reduced pressure, treated with acetonitrile and concentrated under reduced pressure at 35° C. The residue was dissolved in acetonitrile (1 volume) and water (2.25 volumes), and the solids were collected by filtration, washed with a solution of 20% acetonitrile in water and dried. The crude product was triturated with hexanes, filtered, washed with hexanes and dried to provide the desired product, as a solid. MS (ESI) m/z 324.9 [M+2]+.

후처리

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiontreated with acetonitrile
  4. concentrationconcentrated under reduced pressure at 35° C
  5. dissolutionThe residue was dissolved in acetonitrile (1 volume)
  6. filtrationwater (2.25 volumes), and the solids were collected by filtration
  7. washwashed with a solution of 20% acetonitrile in water
  8. customdried
  9. customThe crude product was triturated with hexanes
  10. filtrationfiltered
  11. washwashed with hexanes
  12. customdried

출처 및 근거

ORD 기록
ord-b05c784e2c7d43c8b6e0f70b3d2abbb8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359364B2

반응 노트

불러오는 중…