Ethyl Acetate → HCID 21906727, compound

HRID 1247614Notes

Reaction equation

HRID 1247614 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[CH:19]=[CH:18][N:17]=[C:16](Cl)[C:15]=3[Cl:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].C(OCC)(=O)C>CS(C)=O>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[C:15]=3[Cl:21])=[O:22])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 21906731HCID 21906731, compound

Product 1

HCID 21906727HCID 21906727, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(1-Adamantylmethyl)-2,3-dichloroisonicotinamide (0.4 g) and tert-butyl 3-aminopropylcarbamate (0.4 g) in DMSO (4 ml) were heated in a sealed tube at 160 C for 5 hrs. Ethyl acetate was added and the solution was washed with NaHCO3 solution, water, KHSO4 solution and water. The solution was dried and the solvent was evaporated. The resulting oil was subjected to flash chromatography, using ethyl acetate/hexane as eluant, to give the title compound as a colourless oil (0.41 g).

Workup

  1. washthe solution was washed with NaHCO3 solution, water, KHSO4 solution and water
  2. customThe solution was dried
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9409f1392baa4978a0802fd25c821da4
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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