1,2-Dichloroethane → HCID 68380202, compound

HRID 83686Notes

Reaction equation

HRID 83686 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]([OH:18])=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:44]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(OCC)(=O)C.C(Cl)Cl>[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([C:16]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=3)[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:18])[CH2:53][CH2:52]1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 81531DiisopropylethylamineHCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 68380202HCID 68380202, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added to DCM (5 mL): 1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid (70 mg, 0.245 mmol), DIPEA (0.130 mL, 0.735 mmol), EDC (57 mg, 0.294 mmol), HOBT (45 mg, 0.294 mmol), and 1-benzylpiperazine (0.085 mL, 0.490 mmol). The solution was stirred at rt for 16 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 (30 g silica, 10% EtOAc/hexanes) and triturated with ethyl acetate and hexanes to afford the title compound as a white powder. (Yield: 52 mg, 0.117 mmol, 48%) 1H NMR (400 MHz, CDCl3) δ 7.62, 7.36-7.19, 7.14, 7.02, 6.60, 5.48, 3.62, 3.42, 2.32, 2.03

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 (30 g silica, 10% EtOAc/hexanes)
  5. customtriturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-981a605b6a9e43e6846c5c20426a527e
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

Loading…