1,2-Dichloroethane → HCID 66571629, compound

HRID 83675Notes

Reaction equation

HRID 83675 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.[NH2:52][CH:53]([CH:55]1[CH2:63][C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH2:56]1)[CH3:54]>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]([NH:52][CH:53]([CH:55]3[CH2:63][C:62]4[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=4)[CH2:56]3)[CH3:54])=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 120903721-(2,3-dihydro-1H-inden-2-yl)ethan-1-amineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 66571629HCID 66571629, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added sequentially to DCM (5 mL): 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (109 mg, 0.275 mmol), DIPEA (0.144 mL, 0.825 mmol), EDC (63 mg, 0.330 mmol), HOBT (51 mg, 0.330 mmol), and crude 2-(1-aminoethyl)indane (˜44 mg, 0.275 mmol). The mixture was stirred for 16 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: 59 mg, 0.109 mmol, 40%) 1H NMR (400 MHz, CDCl3) 7.64, 7.31, 7.27-7.09, 7.02, 6.63, 5.45, 5.24, 4.33, 4.17, 3.00, 2.90-2.58, 2.49, 2.29-2.11, 1.83-1.34, 1.18

Workup

  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

Sources & evidence

ORD record
ord-9abe896653124728a8fa7750aafd47e3
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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