Cyanogen Bromide → HCID 59710157, compound

HRID 1864491Notes

Reaction equation

HRID 1864491 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][C@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[N:21]#[C:22]Br>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH3:14])[N:11]([C:22]#[N:21])[C@H:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 59710157HCID 59710157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.00 g of cis-3,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester (prepared according to the method E. Jon Jacobson et. al. J. Med. Chemistry. 1999, Vol. 42, 1123-144) in 91 mL of dichloromethane was treated with sodium bicarbonate (4.7 g) followed by addition of cyanogen bromide (7.5 mL). The reaction mixture was heated at reflux overnight, was filtered, and was purified by column chromatography (0 to 50% ethyl acetate/hexanes) to afford 3.9 g of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ ppm 1.33 (d, 6H, J=6.5 Hz), 1.44 (s, 9H), 2.54 (m, 2H), 3.09 (m, 2H), 4.09 (m, 2H); 13C NMR (CDCl3, 75 MHz) 16.70 (2C), 28.54 (3C), 53.86 (4C), 80.86, 114.10, 154.22.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationwas filtered
  4. customwas purified by column chromatography (0 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aa4825f8e4e9497486c57dc312eece30
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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