1,2-Dichloroethane → HCID 56927671, compound

HRID 83674Notes

Reaction equation

HRID 83674 reaction equation
[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.[CH2:52]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH2:54][CH:53]1[CH2:61][NH2:62]>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[CH2:19][CH2:20][CH:21]([C:24]([NH:62][CH2:61][CH:53]3[CH2:54][C:55]4[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=4)[CH2:52]3)=[O:25])[CH2:22][CH2:23]2)=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22346315(2,3-Dihydro-1H-inden-2-yl)methanamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 56927671HCID 56927671, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added sequentially to DCM (8 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (180 mg, 0.454 mmol), DIPEA (0.317 mL, 1.814 mmol), EDC (96 mg, 0.499 mmol), HOBT (76 mg, 0.499 mmol), and crude (2,3-dihydro-1H-inden-2-yl)methanamine (˜105 mg, 0.713 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×). The organic phase was dried with magnesium sulfate and concentrated in vacuo. Purification was accomplished via silica gel flash chromatography (60 g silica, 50% EtOAc/Hexanes), followed by EtOAc/hexane trituration to give the title compound as a white powder. (Yield: 137 mg, 0.260 mmol, 57%) 1H NMR (400 MHz, CDCl3) 7.66, 7.36-7.14, 7.04, 6.65, 5.55-5.40, 4.35, 3.39, 3.15-3.03, 2.88, 2.71-2.65, 2.31-2.19, 1.74, 1.49

Workup

  1. washdiethyl ether and washed with 1M HCl (1×), 10% aq. sodium carbonate (1×)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-2b0c05178db1421eb805c303a0f00158
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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