Water → HCID 58997014, compound

HRID 251068Notes

Reaction equation

HRID 251068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]([CH2:31]N)[CH2:12][CH:13](CC2C=CC=CN=2)[NH:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20]C(C)=[CH:18][N:17]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:33][C:34]([O-])=O.[Na+].Br[C:39]#[N:40].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[C:12]([CH2:13][N:14]([CH2:15][C:16]3[C:21]([CH3:22])=[CH:20][C:34]([CH3:33])=[CH:18][N:17]=3)[CH2:8][CH2:11][CH2:12][CH2:13][NH:14][C:39]#[N:40])=[N:17][CH:16]=[CH:15][CH:31]=2)([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 131726670HCID 131726670, compound

Product 1

HCID 58997014HCID 58997014, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-{3-[1-(4-chloro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl-N-(3,5-dimethyl-pyridin-2-ylmethyl)-butane-1,4-diamine (0.200 g, 0.444 mmol) in dry MeOH (4 mL), at 0° C., was added NaOAc (0.106 g, 1.29 mmol) and BrCN (0.063 g, 0.59 mmol). The mixture was stirred at 0° C. for 30 min, then at room temperature for 2 h. Water (10 mL) was added, and the mixture was extracted with CH2Cl2 (3×20 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum. The residue was purified by flash chromatography on a silica gel column (100:5:2 CH2Cl2/MeOH/NH4OH), affording a pale yellow oil (0.13 g, 62%). 1H NMR (CDCl3) δ 1.35-1.45 (m, 4H), 1.65 (s, 6H), 1.99 (s, 3H), 2.25 (s, 3H), 2.32-2.40 (m, 2H), 2.62-2.70 (m, 2H), 3.04 (s, 2H), 3.22 (s, 2H), 7.02 (d, 2H, J=8.1 Hz), 7.15-7.28 (m, 4H), 7.91 (d, 1H, J=7.8 Hz), 8.13 (s, 1H), 8.48 (s, br. 1H), 8.57 (d, 1H, J=3.9 Hz). ES-MS m/z 476 (M+H).

Workup

  1. waitat room temperature for 2 h
  2. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed by evaporation under vacuum
  6. customThe residue was purified by flash chromatography on a silica gel column (100:5:2 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-ffdf3160136d4ef884dc1867c0ba6e94
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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