Diisopropylethylamine → tert-Butyl 4-((2-isopropylthiazol-4-yl)methyl)piperazine-1-carboxylate

HRID 416902노트

반응식

HRID 416902 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[S:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C(Cl)Cl.CCOC(C)=O>[CH:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:30]2[CH2:29][CH2:28][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:32][CH2:31]2)[N:4]=1)([CH3:10])[CH3:9]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27631934-(Chloromethyl)-2-isopropyl-1,3-thiazole

생성물 1

HCID 57897180tert-Butyl 4-((2-isopropylthiazol-4-yl)methyl)piperazine-1-carboxylate수율 65%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
35 °C

실험 절차

4-(Chloromethyl)-2-isopropyl-thiazole (0.500 g, 2.85 mmol, 1 eq) was suspended in DCM (4.5 mL). DIPEA (1.24 mL, 7.1 mmol, 2.5 eq) was added dropwise, followed by N-Boc-piperazine (1.170 g, 6.3 mmol, 2.2. eq). The reaction mixture was stirred at 35° C. for 5 h, then diluted with EtOAc, and washed with H2O and brine. The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo. The crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1) to give the title compound as a clear oil (0.600 g, 65%); 1H-NMR (500 MHz, CDCl3): δ 1.39 (d, J=7.0 Hz, 6H, iPr—CH3), 1.46 (s, 9H, C(CH3)3), 2.47 (br t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.34 (m, 1H, iPr—CH), 3.6 (br t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.66 (s, 2H, NCH2), 6.98 (s, 1H, thiazole 5-H); LC (Method B)-MS (ESI, m/z): Rt=2.80 min—326 [(M+H)+, 100%].

후처리

  1. washwashed with H2O and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1)

출처 및 근거

ORD 기록
ord-35cfde9b68d04fb2828c4ce125075240
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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