Phenylmethanesulfonyl chloride → HCID 11606208, compound

HRID 1432432Notes

Reaction equation

HRID 1432432 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:31]=[C:32]([CH:42]4[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]4)[NH:33][C:34]=3[C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=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:31]=[C:32]([CH:42]4[CH2:47][CH2:46][CH:45]([NH:48][S:8]([CH2:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:10])=[O:9])[CH2:44][CH2:43]4)[NH:33][C:34]=3[C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=3)=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11696504HCID 11696504, compound

Product 1

HCID 11606208HCID 11606208, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-Toluenesulfonyl chloride (0.023 g, 0.12 mmol) and diisopropylethylamine (0.026 mL, 0.15 mmol) were added to a solution of 4-[4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl] cyclohexylamine (see Example 19; 0.038 g, 0.10 mmol) 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 (9%) of the title compound as a yellow solid. MS (ESP+) m/z 531.1 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.67 (m, 1H), 7.41 (m, 6H), 7.30 (m, 1H), 7.22 (m, 1H), 7.01 (m, 2H), 6.07 (s, 2H), 4.34 (s, 2H), 3.05 (m, 2H), 2.63 (s, 3H), 2.13 (m, 2H), 1.95 (m, 2H), 1.72 (m, 2H), 1.43 (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-ae87ea2892094a58b299384ecb9a9014
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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