홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Toluene → N-((5-(4-cyano-3-fluorophenyl)pyridin-3-yl)(cyclopropyl)-methyl)ethanesulfonamide

HRID 2407408
노트
인쇄 미리보기

반응식

HRID 2407408 반응식
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:16]=O)[CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH3:19].[NH4+].[Cl-].[C:26]1([CH3:32])C=CC=C[CH:27]=1>C(OCC)(=O)C.[Cl-].[Na+].O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH:32]3[CH2:26][CH2:27]3)[NH:23][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH:13]=[N:12][CH:11]=2)=[CH:9][C:2]=1[F:1])#[N:5]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 73702EthanesulfonamideHCID 595784372-Fluoro-4-(5-formyl-pyridin-3-yl)-benzonitrile

생성물 1

HCID 49820125N-((5-(4-cyano-3-fluorophenyl)pyridin-3-yl)(cyclopropyl)-methyl)ethanesulfonamide수율 30%

시약·촉매·용매 3

HCID 11026
Titanium isopropoxide
촉매
HCID 8857Ethyl Acetate용매
HCID 57417360Sodium chloride; water용매

반응 조건

온도
-36 °C

실험 절차

Titanium isopropoxide (0.98 mL, 3.36 mmol) was added to a mixture of 2-fluoro-4-(5-formyl-pyridin-3-yl)-benzonitrile (380 mg, 1.68 mmol) and ethanesulfonamide (183 mg, 1.68 mmol) in toluene (14 mL) at RT. The resulting mixture was heated to reflux for 2 h. After concentration, the residue was dissolved in THF (100 mL) and a solution of c-PrMgBr (0.5 M in THF, 16.8 mL, 8.40 mmol) was added dropwise at −40° C., and the resulting mixture was stirred at −36° C. for 1 h. Saturated NH4Cl solution was added to the reaction mixture. The resulting mixture was diluted with ethyl acetate and brine, and subsequently filtered. The organic layer was separated to concentrate and purified by flash column (10% MeOH/DCM=0-30%) to give the title compound (185 mg, 30%); ESI-MS m/z: 360 [M+1]+, 1HNMR (MeOD, 400 MHz) δ ppm 8.85 (1H, d, J=2.0 Hz), 8.72 (1H, d, J=2.0 Hz), 8.25 (1H, t, J=2.0 Hz), 7.94 (1H, d, J=8.0 Hz), 7.82-7.77 (2H, m), 3.95 (1H, d, J=9.2 Hz), 3.89 (3H, s), 3.07-2.96 (2H, m), 1.34-1.29 (1H, m), 1.31 (1H, t, J=7.2 Hz), 0.81-0.76 (1H, m), 0.67-0.62 (2H, m), 0.55-0.51 (1H, m)

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in THF (100 mL)
  5. filtrationsubsequently filtered
  6. customThe organic layer was separated
  7. concentrationto concentrate
  8. custompurified by flash column (10% MeOH/DCM=0-30%)

출처 및 근거

ORD 기록
ord-52ce5d8751c6414fa99069e9fa5d9092
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809545B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트