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

HRID 79116

反応式

HRID 79116 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

2-bromothiazole-4carboxylic 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.

後処理

  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

出典と根拠

ORDレコード
ord-28eac06b7a984ea8950dc23d30f3b495
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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