5-Fluoro-2-(trifluoromethyl)benzoyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-[5-fluoro-2-(trifluoromethyl)phenyl]ethanone

HRID 448082노트

반응식

HRID 448082 반응식
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:24]([F:27])([F:26])[F:25])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21]>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:20]([C:19]1[CH:23]=[C:15]([F:14])[CH:16]=[CH:17][C:18]=1[C:24]([F:27])([F:25])[F:26])=[O:21])[CH2:3][CH2:4][CH3:5]

참가 물질

4

반응물 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

생성물 1

HCID 69187211(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-[5-fluoro-2-(trifluoromethyl)phenyl]ethanone

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by 5-fluoro-2-(trifluoromethyl)benzoyl chloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ PPM 0.89 (t, 3 H) 1.28-1.37 (m, 2 H) 1.56-1.63 (m, 2 H) 2.18 (s, 3 H) 2.21 (s, 3 H) 3.90-3.97 (m, 2 H) 5.99 (2, 1 H) 7.36-7.44 (m, 2 H) 7.79-7.83 (m, 1 H); MS (ESI) m/z 374 (M+H)+.

후처리

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-fc8b07186f234f62ad212ce64fccf7a7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481574B2

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