1,2-Dichloroethane → HCID 66570887, compound

HRID 83685Notes

Reaction equation

HRID 83685 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][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](O)=[O:17])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:44]1[CH2:49][CH2:48][CH:47]([CH2:50][N:51]2[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH2:46][CH2:45]1>C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][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:44]2[CH2:45][CH2:46][CH:47]([CH2:50][N:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[CH2:48][CH2:49]2)=[O:17])=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 128029051-(Piperidin-4-ylmethyl)piperidineHCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 66570887HCID 66570887, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added to DCM (6 mL): 1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid (110 mg, 0.380 mmol), DIPEA (0.5 mL, 2.95 mmol), EDC (100 mg, 0.506 mmol), HOBT (80 mg, 0.506 mmol), and 1-(piperidin-4-ylmethyl)piperidine (150 mg, 0.843 mmol). The solution was stirred at rt for 15 h, at which time the solution was diluted with a 1:1 solution of ethyl acetate:diethyl ether and washed with water (1×), 10% aq. sodium carbonate (1×), and brine (1×). The organic phase was then dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified via silica gel flash chromatography (40 g silica, 10% EtOAc/hexanes) and triturated with ethyl acetate and hexanes to afford the title compound as a white powder. (Yield: 109 mg, 0.242 mmol, 70%) 1H NMR (400 MHz, CDCl3) δ 7.63, 7.35, 7.23-7.12, 7.03, 6.59, 5.46, 4.59, 4.09, 2.75, 2.34, 2.08, 1.71-1.46, 1.46-1.36

Workup

  1. washdiethyl ether and washed with water (1×), 10% aq. sodium carbonate (1×), and brine (1×)
  2. dry with materialThe organic phase was then dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified via silica gel flash chromatography (40 g silica, 10% EtOAc/hexanes)
  5. customtriturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-fd09bc05c51742f580f71b6ff4d5fe5e
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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