tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-bromothiazole-4-carbonyl)piperazine-1-carboxylate

HRID 875947

반응식

HRID 875947 반응식
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[O:9])[N:6]=1

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

생성물 1

HCID 58299784Tert-butyl 4-(2-bromothiazole-4-carbonyl)piperazine-1-carboxylate수율 92.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

2-bromothiazole-4-carboxylic acid (1.31 g, 6.3 mmol) was combined with tert-butyl piperazine-1-carboxylate (1.2 g, 6.3 mmol) in DCM (15 mL), and then stirred at 20° C. until it formed a clear solution. N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.2 g, 6.3 mmol) was then added, and the reaction was stirred at 20° C. for 2 hours. The reaction was concentrated in vacuum, before transferring it to a separation funnel with ethyl acetate. The organic layer was washed with saturated NaHCO3, water, NH4Cl, and then with brine. After drying the organic layer with MgSO4, it was concentrated in vacuum to yield compound 72 (2.2 g, 91%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.16 (1H, s), 3.61 (4H, m), 3.38 (4H, m), 1.42 (9H, s) ppm; LCMS-ESI (POS), M/Z, M+1−C3H9: Found 320.0.

후처리

  1. customformed a clear solution
  2. stirringthe reaction was stirred at 20° C. for 2 hours
  3. concentrationThe reaction was concentrated in vacuum
  4. washThe organic layer was washed with saturated NaHCO3, water, NH4Cl
  5. dry with materialAfter drying the organic layer with MgSO4, it
  6. concentrationwas concentrated in vacuum

출처 및 근거

ORD 기록
ord-2154549b26b14482bfd0050cfbf9bf59
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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