Diisopropylethylamine → Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)thiazole-4-carboxylate

HRID 1486820노트

반응식

HRID 1486820 반응식
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[CH3:10][O:9][C:7]([C:5]1[N:6]=[C:2]([N:21]2[CH2:20][CH2:19][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:23][CH2:22]2)[S:3][CH:4]=1)=[O:8]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 7213135Methyl 2-chloro-4-thiazolecarboxylate

생성물 1

HCID 89873086Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)thiazole-4-carboxylate수율 35.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
150 °C

실험 절차

Methyl 2-chlorothiazole-4-carboxylate (500 mg, 2.82 mmol), N-Boc-piperazine (655 mg, 3.52 mmol) and DIPEA (736 uL, 4.22 mmol) were dissolved in DMA (10 mL) and the reaction mixture was heated in a microwave reactor at 150° C. for 45 min. The reaction mixture was partitioned between EtOAc (40 mL) and water (40 mL) and the organic fraction was washed with water (40 mL) and brine (40 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a white solid (324 mg, 35.1%). LCMS (ES+): 350.1 [MNa]+. HPLC: Rt 6.04 min, 100% purity.

후처리

  1. customThe reaction mixture was partitioned between EtOAc (40 mL) and water (40 mL)
  2. washthe organic fraction was washed with water (40 mL) and brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a76bb42cf1ee4014bcbab54d8eb8113a
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428498B2

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