Phenylmethanesulfonyl chloride → HCID 10481670, compound

HRID 1432424Notes

Reaction equation

HRID 1432424 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:30]3[N:34]=[C:33]([CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[NH:32][C:31]=3[C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=3)=[CH:29][C:24]=2[O:23][CH2:22]1>C1COCC1>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:30]3[N:34]=[C:33]([CH:35]4[CH2:36][CH2:37][N:38]([S:8]([CH2:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:10])=[O:9])[CH2:39][CH2:40]4)[NH:32][C:31]=3[C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=3)=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11703265HCID 11703265, compound

Product 1

HCID 10481670HCID 10481670, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-Toluenesulfonyl chloride (0.032 g, 0.17 mmol) and diisopropylethylamine (0.036 mL, 0.21 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 (0.050 g, 0.14 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 0.005 g (7%) of the title compound as a yellow solid. MS (ESP+) m/z 517.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.73 (t, 1H, J=7.7 Hz), 7.42 (m, 5H), 7.33 (d, 1H, J=7.3 Hz), 7.27 (d, 1H, J=7.3 Hz), 6.07 (s, 2H), 4.40 (s, 2H), 3.82 (m, 2H), 3.19 (m, 1H), 2.85 (m, 2H), 2.66 (s, 3H), 2.10 (m, 2H), 1.92 (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-2421169721a44f3d8a158cf961bcd5ef
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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