Triethylamine → 3-cyano-N-{3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-benzenesulfonamide

HRID 1182133Notes

Reaction equation

HRID 1182133 reaction equation
Cl.[F:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.Br[CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=1)(=[O:21])=[O:20].C(N(CC)CC)C>C(#N)C>[C:28]([C:24]1[CH:23]=[C:22]([S:19]([NH:18][CH2:17][CH2:16][CH2:15][N:10]2[CH2:9][CH:8]([O:7][C:6]3[CH:12]=[CH:13][C:3]([F:2])=[CH:4][CH:5]=3)[CH2:11]2)(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=1)#[N:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochlorideHCID 43133728N-(3-bromopropyl)-3-cyano-benzenesulfonamide

Product 1

HCID 102374953-cyano-N-{3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of 3-(4-fluoro-phenoxy)-azetidine hydrochloride (0.049 g, 0.24 mmol) in acetonitrile (1.0 ml) is treated with the crude N-(3-bromo-propyl)-3-cyano-benzenesulfonamide (0.072 g) in acetonitrile (1.0 ml) and triethylamine (0.1 ml, 0.72 mmol). The resulting homogenous reaction mixture is stirred at ambient temperature for 70 hours, the solvent evaporated and the residue partitioned between ethylacetate and aqueous NaHCO3 solution. The ethylacetate phase is washed with brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution ethylacetate) to afford 3-cyano-N-{3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-benzenesulfonamide. [MH]+ 390.

Workup

  1. customthe solvent evaporated
  2. customthe residue partitioned between ethylacetate and aqueous NaHCO3 solution
  3. washThe ethylacetate phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (elution ethylacetate)

Sources & evidence

ORD record
ord-636f502fba204a8b86f6bfcfe74acef6
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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