Phenylmethanesulfonyl chloride → HCID 10345947, compound

HRID 1432425Notes

Reaction equation

HRID 1432425 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]=[CH:43][N:42]=3)=[CH:29][C:24]=2[O:23][CH2:22]1.C(OC(N1CCC(C2NC(C3C=CC=CN=3)=C(C3C=CC4OCOC=4C=3)N=2)CC1)=O)C1C=CC=CC=1>>[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]=[CH:43][N:42]=3)=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

5

Reactant 4

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11583875HCID 11583875, compoundHCID 11638826HCID 11638826, compound

Product 1

HCID 10345947HCID 10345947, compoundYield 10%

Procedure

α-Toluenesulfonyl chloride (0.023 g, 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, in 3 mL of anhydrous THF), which was prepared with 4-(4-benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester in a similar manner as described in Example 9. 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 (10%) of the title compound as a yellow solid. MS (ESP+) m/z 503.1 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 8.67 (m, 1H), 7.82 (m, 1H), 7.42 (m. 7H), 7.02 (m, 3H), 6.07 (s, 2H), 4.38 (s, 2H), 3.81 (m, 2H), 3.17 (m, 1H), 2.85 (m, 1H), 2.10 (m, 2H), 1.90 (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-988b0f87b4dc47d7b54472bb3cc8bafa
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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