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Diisopropylethylamine → Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1502082
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HRID 1502082 반응식
Br[CH2:2][C:3]([C:5]1[C:6]([CH3:14])=[C:7]([C:10]([F:13])=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[OH:15][CH2:16][CH2:17][CH:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1.CCN(C(C)C)C(C)C>C1COCC1.[Cl-].[Na+].O>[C:8]([C:7]1[C:6]([CH3:14])=[C:5]([C:3](=[O:4])[CH2:2][N:23]2[CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:19][CH:18]2[CH2:17][CH2:16][OH:15])[CH:12]=[CH:11][C:10]=1[F:13])#[N:9]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylateHCID 867270493-(2-Bromo-acetyl)-6-fluoro-2-methyl-benzonitrile

생성물 1

HCID 89619114Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 57417360
Sodium chloride; water
용매

실험 절차

3-(2-Bromoacetyl)-6-fluoro-2-methylbenzonitrile (prepared as described above, 5.11 g, 20.0 mmol) was dissolved in THF (100 mL), then known, commercially available compound tert-butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate (4.60 g, 20.0 mmol) was added, followed by Hunig's base (6.96 mL, 39.9 mmol) and the mixture was stirred overnight. The reaction mixed was poured into brine and extracted with ethyl acetate (twice), dried over Na2SO4, filtered and concentrated. The product was purified by MPLC chromatography using a 330 g ISCO Redi Sep column and 5% MeOH/DCM solvent system-to yield tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate: LC-MS (IE, m/z): 406 [M+1]+;

후처리

  1. additionThe reaction mixed
  2. extractionextracted with ethyl acetate (twice),
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by MPLC chromatography

출처 및 근거

ORD 기록
ord-595fc8d3918c4789823db85ea7012c2d
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206199B2

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