Acetonitrile → HCID 68522134, compound

HRID 1992403Notes

Reaction equation

HRID 1992403 reaction equation
Cl.Cl.[C:3]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][S:11]([CH2:14][CH2:15][N:16]2[CH2:23][CH:22]3[O:24][CH:18]([CH2:19][NH:20][CH2:21]3)[CH2:17]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)#[N:4].Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][S:11]([CH2:14][CH2:15][N:16]2[CH2:23][CH:22]3[O:24][CH:18]([CH2:19][N:20]([CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=4)[CH2:21]3)[CH2:17]2)(=[O:13])=[O:12])=[CH:25][CH:26]=1)#[N:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5731291-(2-Bromoethyl)-3-fluorobenzeneHCID 68522681HCID 68522681, compound

Product 1

HCID 68522134HCID 68522134, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To 2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethanesulfonic acid 4-cyano-benzylamide dihydrochloride (0.127 g, 0.30 mmol; prep P above), 1-(2-bromo-ethyl)-3-fluoro-benzene (0.064 g, 0.315 mmol) and potassium carbonate (0.145 g, 1.05 mmol) was added acetonitrile (4 mL) and water (0.1 mL). The mixture was stirred for 20 minutes before it was heated by microwave irradiation (10 minutes, 160° C.) and was then filtered and evaporated. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 43 mg (30.3%) of the title compound.

Workup

  1. filtrationwas then filtered
  2. customevaporated
  3. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f6494dc53df64d0bb17769187195261c
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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