1,2-Dichloroethane → HCID 66571159, compound

HRID 83615Notes

Reaction equation

HRID 83615 reaction equation
[F: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>CCOCC.CCOC(C)=O.CN(C=O)C>[F: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

9

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 128029051-(Piperidin-4-ylmethyl)piperidineHCID 186270691-(4-fluorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 66571159HCID 66571159, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was added to anhydrous DMF (2 mL) sequentially: 1-(4-fluorobenzyl)-1H-indole-2-carboxylic acid (66.8 mg, 0.248 mmol), Hunig's Base (0.217 ml, 1.240 mmol), EDC (52.3 mg, 0.273 mmol), HOBT (41.8 mg, 0.273 mmol), and 1-(piperidin-4-ylmethyl)piperidine (45.2 mg, 0.248 mmol) (from SJB-2-083.) This was stirred at room temperature for 24 h with 3 Å MS. At this time, a 1:1 solution of EtOAc:Et2O was added and the solution was washed with 10% aq. Na2CO3. The organic phase was dried with MgSO4 and concentrated in vacuo. The residue was then purified by silica gel chromatography (20 g silica, 80% EtOAc/Hexanes) to give 58 mg of the title compound as an oil.

Workup

  1. washthe solution was washed with 10% aq. Na2CO3
  2. dry with materialThe organic phase was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was then purified by silica gel chromatography (20 g silica, 80% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-44aac94db3cf41a589a1708213bec840
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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