1,2-二氯乙烷 → (1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(2-phenylpyrrolidine-1-carbonyl)piperidin-1-yl)methanone

HRID 83671

反应方程式

HRID 83671 反应方程式
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:52]1([CH:58]2[CH2:62][CH2:61][CH2:60][NH:59]2)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([N:59]3[CH2:60][CH2:61][CH2:62][CH:58]3[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

参与物

8

反应物 5

HCID 111,2-二氯乙烷HCID 757711-羟基苯并三唑(HOBT)HCID 81531N,N-二异丙基乙胺HCID 2618922-苯基吡咯烷HCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

产物 1

HCID 66571627(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(2-phenylpyrrolidine-1-carbonyl)piperidin-1-yl)methanone

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂HCID 8857乙酸乙酯溶剂

实验过程

The following was added sequentially to DCM (2 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (50 mg, 0.126 mmol), DIPEA (0.07 mL, 0.378 mmol), EDC (30 mg, 0.151 mmol), HOBT (24 mg, 0.151 mmol), and 2-phenylpyrrolidine (0.023 mL, 0.151 mmol). The mixture was stirred for 18 h at rt, at which time the solution diluted with a 1:1 solution of ethyl acetate:diethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×). The organic phase was dried with magnesium sulfate and concentrated in vacuo. The resulting residue was dissolved in EtOAc and precipitated out hexanes, and then collected over a filter and washed with diethyl ether to give the title compound as a white solid. (Yield: 20 mg, 0.038 mmol, 30%) 1H NMR (400 MHz, CDCl3) 7.61, 7.43-7.05, 7.09-6.94, 6.58, 5.41, 5.06-4.82, 4.33, 3.83-3.60, 3.11-2.88, 2.50-2.22, 2.06-1.58, 1.16-0.82

后处理

  1. washdiethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×) and brine (1×)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in EtOAc
  5. customprecipitated out hexanes
  6. customcollected over
  7. filtrationa filter
  8. washwashed with diethyl ether

来源与证据

ORD记录
ord-eaaf5c319cdc4f1a8e5249115a01e03b
来源数据集
uspto-grants-2014_09
专利号
US08846684B2

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