Diisopropylethylamine → US10385022, Example 6

HRID 877964노트

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HRID 877964 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:6]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

생성물 1

HCID 60197094US10385022, Example 6수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Fluoro-5-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 171243-30-4) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). After 2 h, an additional 25 μL of acyl chloride was added. The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (45 mg, 57%). MS (ESI): m/z=470.0 [M+H]+.

후처리

  1. filtrationfiltered
  2. customall volatiles removed
  3. customThe resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane

출처 및 근거

ORD 기록
ord-af7b6bb4788242359edbb2b600642689
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

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