Methanesulfonyl chloride → HCID 10455927, compound

HRID 1432427Notes

Reaction equation

HRID 1432427 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].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][NH:32][CH2:31][CH2:30]4)[NH:26][C:25]=3[C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=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[CH2:30][CH2:31][N:32]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:33][CH2:34]4)[NH:26][C:25]=3[C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=3)=[CH:23][C:18]=2[O:17][CH2:16]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11703265HCID 11703265, compound

Product 1

HCID 10455927HCID 10455927, compoundYield 25%

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)-6-methyl-pyridine (0.036 g, 0.10 mmol; see Example 9) 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 0.011 g (25%) of the title compound as a yellow solid. MS (ESP+) m/z 441.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.74 (t, 1H, J=7.9 Hz), 7.34 (m, 1H), 7.28 (m, 1H), 7.03 (m, 3H), 6.08 (s, 2H), 3.92 (m, 2H), 3.25 (m, 1H), 2.94 (m, 2H), 2.90 (s, 3H), 2.66 (s, 3H), 2.23 (m, 2H), 2.03 (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-2d2ff49f556a4764ad15fd26f8e26f22
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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