Triethylamine → (R)-N-(3-(1-(6-chloropyrazin-2-yloxy)ethyl)phenyl)-3-(trifluoromethyl)benzamide

HRID 1255852노트

반응식

HRID 1255852 반응식
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])[CH3:10])[CH:5]=[N:4][CH:3]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](O)=[O:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C:11]2[CH:12]=[C:13]([NH:14][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=3)[CH:15]=[CH:16][CH:17]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 99633-(Trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86641863(R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline

생성물 1

HCID 86641864(R)-N-(3-(1-(6-chloropyrazin-2-yloxy)ethyl)phenyl)-3-(trifluoromethyl)benzamide수율 40.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline (160 mg, 0.64 mmol), 3-trifluoromethylbenzoic acid (183 mg, 0.96 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (246 mg, 1.28 mmol), 4-dimethylamino pyridine (4 mg, 0.032 mmol) and triethylamine (0.36 mL, 2.57 mmol) in dichloromethane (6 mL) was stirred at room temperature for 18 hours. After this time the mixture was diluted with dichloromethane (30 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×20 mL) and brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give (R)—N-(3-(1-(6-chloropyrazin-2-yloxy)ethyl)phenyl)-3-(trifluoromethyl)benzamide (110 mg, 30% over 2 steps) as a yellow foam.

후처리

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate (2×20 mL) and brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give an orange oil which
  5. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-c4762a9966c145e48651640f7ce3441f
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461161B2

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