Potassium Carbonate → HCID 9802767, compound

HRID 1992333Notes

Reaction equation

HRID 1992333 reaction equation
[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[CH2:2]2.Br[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][N:7]1[CH2:8][CH:1]2[O:9][CH:5]([CH2:4][N:3]([CH2:10][CH2:11][CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH2:2]2)[CH2:6]1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate2×HCID 18540400HCID 18540400, compound

Product 1

HCID 9802767HCID 9802767, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-[3-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propoxy]benzonitrile (6.5 g, 0.0226 mol; see WO 01/28992) and tert-butyl 2-bromoethylcarbamate (6 g, 0.0271 mol; see WO 01/28992) were dissolved in 80 mL of dry acetonitrile. Anhydrous potassium carbonate (4.68 g, 0.034 mol) was added and the mixture was stirred at 60° C. overnight. A further portion of tert-butyl 2-bromoethylcarbamate (2.53 g, 0.0113 mol) was added and the reaction heated at 65° C. overnight. The reaction mixture was then filtered and the filtrate concentrated under reduced pressure. The product was purified by column chromatography using methanol-chloroform as eluent to give the sub-title compound (4.5 g) as a yellow solid.

Workup

  1. temperaturethe reaction heated at 65° C. overnight
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e34089578e16492ab6335ae3d2c49f74
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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