Tetrahydrofuran → Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate

HRID 1361474노트

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HRID 1361474 반응식
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])=O.C(N(C(C)C)CC)(C)C.C1COCC1>O>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:22]1[N:2]=[C:1]([N:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9]2)[S:3][CH:21]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 27374492-Bromo-2'-fluoroacetophenoneHCID 57354701Benzyl 4-carbamothioylpiperazine-1-carboxylate

생성물 1

HCID 15984569Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate수율 27.2%

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A solution of benzyl 4-thiocarbamoylpiperazine-1-carboxylate (2.7 g, 9.7 mmol), 2-bromo-1-(2-fluorophenyl)ethanone (2.1 g, 9.7 mmol), diisopropyl ethylamine (1.9 mL, 11 mmol), and THF (32 mL) was sealed in a microwave vessel and heated by microwave irradiation at 120° C. for 20 seconds. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 0%-30% EtOAc/hexanes) to give benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate (1.05 g, 27% yield). LC/MS: m/z 398.3 (M+H)+ at 3.84 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, 0%-30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-6e06895041ca427285a61324089d917e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880008B2

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