Methanesulfonyl chloride → HCID 11704573, compound

HRID 1432426Notes

Reaction equation

HRID 1432426 reaction equation
CS(Cl)(=O)=O.C(N(C(C)C)CC)(C)C.[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][N:32]([S:35]([CH2:38]C5C=CC=CC=5)(=[O:37])=[O:36])[CH2:31][CH2:30]4)[NH:26][C:25]=3[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:23][C:18]=2[O:17][CH2:16]1>C1COCC1>[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]4)[NH:26][C:25]=3[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:23][C:18]=2[O:17][CH2:16]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10345947HCID 10345947, compound

Product 1

HCID 11704573HCID 11704573, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.009 mL, 0.12 mmol) and diisopropylethylamine (0.026 mL, 0.15 mmol) were added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.035 g, 0.10 mmol; prepared as described in Example 11) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 3 hours. Solvent was removed under reduced pressure, and the residue was dissolved in 1 mL DMSO. The DMSO solution was filtered and injected onto preparative HPLC. HPLC purification eluting with acetonitrile:water gave 0.012 g (28%) of the title compound as a yellow solid. MS (ESP+) m/z 427.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.65 (m, 1H), 7.83 (m, 1H), 7.56 (m, 1H), 7.45 (m. 1H), 7.03 (dd, 1H, J=1.8 Hz, 8.1 Hz), 6.97 (d, 1H, J=1.8 Hz), 6.88 (d, 1H, d=8.1 Hz), 6.05 (s, 2H), 3.91 (m, 2H), 3.47 (m, 1H), 2.89 (m, 2H), 2.84 (s, 3H), 2.22 (m, 2H), 2.11 (m, 2H).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 1 mL DMSO
  3. filtrationThe DMSO solution was filtered
  4. customHPLC purification
  5. washeluting with acetonitrile

Sources & evidence

ORD record
ord-862cbc4a96c74eeb88498d76728788c8
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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