Benzothiazole → 4-(Benzo[d]thiazol-2-yl(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile

HRID 2104948노트

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HRID 2104948 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([O:35][CH:36]([CH3:38])[CH3:37])[C:21]([F:34])=[C:22]([CH:33]=1)/[CH:23]=[N:24]/[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1)[CH3:16]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:24]([CH2:23][C:22]1[CH:33]=[C:18]([O:17][CH2:15][CH3:16])[CH:19]=[C:20]([O:35][CH:36]([CH3:38])[CH3:37])[C:21]=1[F:34])[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 7222BenzothiazoleHCID 178418339ButyllithiumHCID 178466720HCID 178466720, 화합물

생성물 1

HCID 688166324-(Benzo[d]thiazol-2-yl(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile수율 42.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

To a solution of benzothiazole (61.9 mg, 0.458 mmol) in 2 mL THF at −78° C. was added 1.6 M solution of BuLi in THF (315 μL, 0.504 mmol). The mixture was stirred at −78° C. for 45 min, then a solution of Intermediate 7.3 (149 mg, 0.458 mmol) in 0.5 mL THF was added dropwise. The mixture was stirred and allowed to warm to rt overnight, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford 90 mg of Intermediate 7.4 as a white solid.

후처리

  1. stirringThe mixture was stirred
  2. temperatureto warm to rt overnight
  3. customwas quenched with sat. NH4Cl
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient)

출처 및 근거

ORD 기록
ord-5b91879fcf2842bc87e613742167ebbb
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576098B2

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