Water → HCID 21906691, compound

HRID 1247602Notes

Reaction equation

HRID 1247602 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].[C:8]12([CH2:18][NH:19][C:20](=[O:29])[C:21]3[C:26]([Cl:27])=[CH:25][N:24]=[C:23](Br)[CH:22]=3)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[C:30](=[O:33])([O-])[O-:31].[K+].[K+].O>CN1CCCC1=O>[C:8]12([CH2:18][NH:19][C:20]([C:21]3[C:26]([Cl:27])=[CH:25][N:24]=[C:23]([N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6][NH:7][C:30](=[O:33])[O:31][C:8]([CH3:17])([CH3:15])[CH3:9])[CH:22]=3)=[O:29])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

6

Reactant 4

HCID 962WaterHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 11430Potassium CarbonateHCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

Product 1

HCID 21906691HCID 21906691, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

N-(2-Hydroxyethyl)-ethylenediamine (0.208 g) was added to a mixture of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (0.192 g, Example 1(ii)) and potassium carbonate (0.14 g) in anhydrous N-methyl-2-pyrrolidinone (3 ml). The resulting solution heated in a MARS microwave for 10 minutes (300 Watts, 150° C.). The mixture was cooled and poured into water (50 ml) and extracted into ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (2×10 ml), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved into ethyl acetate 30 ml and di-tert-butylcarbonate (0.218 g) added. The resulting mixture was left to stand at room temperature for 2 hours and was then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with ethyl acetate to afford tert-butyl 2-[(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)(2-hydroxyethyl)amino]ethylcarbamate (0.013 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted into ethyl acetate (3×10 ml)
  3. washThe combined organic extracts were washed with brine (2×10 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved into ethyl acetate 30 ml and di-tert-butylcarbonate (0.218 g)
  8. additionadded
  9. waitThe resulting mixture was left
  10. concentrationwas then concentrated under reduced pressure
  11. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-56425a353c9b406fa7904b4122e5da17
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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