Ethylenediamine → HCID 86751684, compound

HRID 1938151Notes

Reaction equation

HRID 1938151 reaction equation
[CH:1]([N:4]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[CH2:5][C:6]#[C:7][CH2:8][NH:9][C:10]([C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:11])([CH3:3])[CH3:2].C(N)CN.[BH4-].[Na+]>C(O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[CH:1]([N:4]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[CH2:5][CH:6]=[CH:7][CH2:8][NH:9][C:10]([C:12]12[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2)=[O:11])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 86751685HCID 86751685, compound

Product 1

HCID 86751684HCID 86751684, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of adamantane-1-carboxylic acid (4-{isopropyl-[2-(2-methoxyphenyl)ethyl]amino}but-2-ynyl)amide, (90 mg, 0.21 mmol), nickel chloride hexahydrate (60 mg, 0.25 mmol), ethylenediamine (0.15 ml, 0.25 mmol) and sodium borohydride (0.25 ml 1N solution in EtOH, 0.25 mmol) in 5 ml ethanol was stirred at ambient temperature for 10 h. The mixture was filtered, the solvent removed and the residue taken up in methylene chloride and washed with water. Evaporation of the solvent gave 71 mg of an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed
  3. washwashed with water
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cb410290233e46ce8da19ce652fc8d0d
Source dataset
uspto-grants-1997_12
Patent number
US05693630

Reaction notes

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