Triethylamine → HCID 178448482, 화합물

HRID 340654노트

반응식

HRID 340654 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:16]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[S:18][C:17]1=[NH:25])[CH2:13][C:14]#[CH:15].[F:26][C:27]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:28]=1[C:29](Cl)=[O:30].C(N(CC)CC)C>C(Cl)Cl>[C:21]([C:19]1[S:18]/[C:17](=[N:25]\[C:29](=[O:30])[C:28]2[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:27]=2[F:26])/[N:16]([CH2:12][CH2:13][C:14]#[CH:15])[CH:20]=1)([CH3:22])([CH3:24])[CH3:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 86644542HCID 86644542, 화합물

생성물 1

HCID 178448482HCID 178448482, 화합물수율 91.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-(but-3-ynyl)-5-tert-butylthiazol-2(3H)-imine p-toluenesulfonate (prepared as described in US20080242654) (2.6 g, 6.83 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl chloride (1.55 g, 6.83 mmol) in anhydrous CH2Cl2 (30 mL) was treated dropwise at 0° C. with triethylamine (1.91 mL, 1.38 mmol). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with hexane-EtOAc (2:1) to afford 2.5 g of the title compound. MS (DCI/NH3) m/z 399 (M+H)+.

후처리

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with hexane-EtOAc (2:1)

출처 및 근거

ORD 기록
ord-fa000a7de4b846c38da818ad1adff5b8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895592B2

반응 노트

불러오는 중…