1-羟基苯并三唑(HOBT) → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-2-yl)ethyl)piperidine-4-carboxamide

HRID 83618

反应方程式

HRID 83618 反应方程式
Cl.C(N=C=NCCCN(C)C)C.N1(O)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([OH:48])=O)[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C.[N:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[CH2:66][CH2:67][NH2:68]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([NH:68][CH2:67][CH2:66][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][N:60]=3)=[O:48])[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1

参与物

9

反应物 5

HCID 757711-羟基苯并三唑(HOBT)HCID 759192-(2-氨乙基)吡啶HCID 81531N,N-二异丙基乙胺HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

产物 1

HCID 665712761-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-2-yl)ethyl)piperidine-4-carboxamide

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂2 次HCID 8857乙酸乙酯溶剂

实验过程

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (235 mg, 1.228 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (166 mg, 1.228 mmol), and 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (390 mg, 0.982 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred for ten minutes before adding N-ethyl-N-isopropylpropan-2-amine (0.214 ml, 1.228 mmol) and 2-(pyridin-2-yl)ethanamine (100 mg, 0.819 mmol) as a 1.0 mL DCM solution. The reaction was stirred overnight at room temperature. It was diluted with water and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ether and ethyl acetate and filtered to obtain white solid as a product. 1H-NMR (400 MHz, DMSO-d6) 8.46, 7.84, 7.66, 7.60, 7.51, 7.37-7.27, 7.24-7.14, 7.12-7.03, 6.69, 5.46, 4.58-3.75, 3.37, 3.12-2.67, 2.34-2.25, 1.59, 1.33

后处理

  1. stirringThe reaction was stirred overnight at room temperature
  2. washThe organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was triturated with ether and ethyl acetate
  7. filtrationfiltered
  8. customto obtain white solid as a product

来源与证据

ORD记录
ord-ca1b81ceb127419fb23845b8dcf45c21
来源数据集
uspto-grants-2014_09
专利号
US08846684B2

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