1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-3-methyl piperazin-2-one

HRID 467543노트

반응식

HRID 467543 반응식
C(N(CC)C(C)C)(C)C.[CH3:10][CH:11]1[NH:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([O:59]C)[CH:42]=1)[CH3:40]>ClCCl.O>[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50]([N:16]3[CH2:15][CH2:14][NH:13][C:12](=[O:17])[CH:11]3[CH3:10])=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([OH:59])[CH:42]=1)[CH3:40]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 51066003-Methyl-2-ketopiperazineHCID 671160464-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid

생성물 1

HCID 513567694-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-3-methyl piperazin-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

N,N-Diisopropylethylamine (74 μL, 0.42 mmol), 3-methylpiperazin-2-one (23.3 mg, 0.20 mmol), EDCI (39.1 mg, 0.20 mmol) and HOBt (27.6 g, 0.20 mmol) were successively added to a suspension of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid (which may be prepared in accordance with the experimental described in Example 4, step 4; 50 mg, 0.17 mmol) in dichloromethane (0.55 mL). The reaction mixture was stirred at room temperature overnight then diluted by addition of dichloromethane (10 mL) and water (10 mL). After separation, the organic layer was washed with water (10 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (98:2 to 95:5) as eluent. The title product was obtained as a white solid (24 mg, 36%).

후처리

  1. custommay be prepared in accordance with the
  2. customAfter separation
  3. washthe organic layer was washed with water (10 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-38d5c65b873240e484ceb314d129b9d6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623865B2

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