Methanesulfonyl chloride → 2-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrile

HRID 513963노트

반응식

HRID 513963 반응식
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[CH:11]=2)(=O)=O.FC1C=C(C=CC=1F)COC1C=C2C(C=C(CO)C=N2)=[N:35][CH:34]=1.CS(Cl)(=O)=O>C(Cl)Cl>[F:26][C:21]1[CH:20]=[C:19]([CH2:18][O:17][C:12]2[CH:11]=[C:10]3[C:15]([CH:16]=[C:7]([CH2:6][C:34]#[N:35])[CH:8]=[N:9]3)=[N:14][CH:13]=2)[CH:24]=[CH:23][C:22]=1[F:25]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 86301659(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanolHCID 90418375(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate

생성물 1

HCID 863016602-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrile수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate. To a solution of (7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanol (Example 73, 90 mg, 0.3 mmol) in DCM (4 mL) was added methanesulfonyl chloride (0.05 mL, 0.61 mmol) followed by TEA (0.06 mL, 0.43 mmol). The reaction mixture was stirred at RT for 1 h and quenched with saturated NaHCO3 solution. The mixture was extracted with DCM (2×) and the combined organic layers were dried, filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 0-80%, EtOAc/hexanes) afforded the title compound as a white solid (73 mg, 64%). [M+H]=381.1.

후처리

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe mixture was extracted with DCM (2×)
  3. customthe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification (FCC, SiO2, 0-80%, EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a99bad42efcb4236a01f49892c1855d7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102674B2

반응 노트

불러오는 중…