Triethylamine → 3-cyano-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)benzenesulfonamide

HRID 1397257Notes

Reaction equation

HRID 1397257 reaction equation
CCN(CC)CC.[C:8]1([C:14]2[N:15]=[C:16]([C:19]3([CH2:25][NH2:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[S:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:27]([C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1)#[N:28]>C(Cl)Cl>[C:27]([C:29]1[CH:30]=[C:31]([S:35]([NH:26][CH2:25][C:19]2([C:16]3[S:17][CH:18]=[C:14]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:15]=3)[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1)#[N:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 699492703-cyano-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)benzenesulfonamideYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Et3N (0.15 mL, 1.43 mmol) was added dropwise to an ice cold solution of (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (130 mg, 0.48 mmol) in dry CH2Cl2 (3 mL). The resulting reaction mixture was stirred at 0° C. for 5 min, then a solution of 3-cyanobenzene-1-sulfonyl chloride (105 mg, 0.52 mmol) in dry CH2Cl2 (2 mL) was added dropwise. The reaction mixture was further stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60-120 mesh, eluent 35% EtOAc in petroleum ether) to afford compound 3-cyano-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)benzenesulfonamide (0.13 g, yield 61%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.03-7.98 (m, 2H), 7.85-7.76 (m, 3H), 7.59-7.54 (m, 1H), 7.50-7.38 (m, 4H), 3.87-3.79 (m, 2H), 3.74-3.66 (m, 2H), 3.36 (s, 2H), 2.27-2.19 (ddd, J=13.5 Hz, 6.7 Hz, 3.5 Hz, 2H), 2.01-1.93 (ddd, J=13.8 Hz, 7.5 Hz, 3.7 Hz, 2H). MS (ESI) m/z: Calculated for C22H21N3O3S2: 439.10. found: 440.0 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was further stirred at room temperature for 1 h
  3. washthe organic layer was washed with H2O and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 60-120 mesh, eluent 35% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fc7fe4beeaea4f2bb93723b426c030d1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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