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

HRID 1486820ノート

反応式

HRID 1486820 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a76bb42cf1ee4014bcbab54d8eb8113a
出典データセット
uspto-grants-2016_08
特許番号
US09428498B2

反応ノート

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