Hydrochloric Acid → 2-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzenesulfonamide

HRID 1992124Notes

Reaction equation

HRID 1992124 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][CH:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[CH2:22][CH2:21][N:20]([C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[S:31]([NH:34]C(=O)OC(C)(C)C)(=[O:33])=[O:32])=[O:24])[CH2:19][CH2:18]4)[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:48]=[CH:49][CH:50]=[CH:51][C:4]=2[N:3]=1.Cl>O1CCOCC1>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][CH:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[CH2:22][CH2:21][N:20]([C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[S:31]([NH2:34])(=[O:33])=[O:32])=[O:24])[CH2:19][CH2:18]4)[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:48]=[CH:49][CH:50]=[CH:51][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58728709tert-butyl {2-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenyl piperidin-1-yl)carbonyl]phenyl}sulfonylcarbamate

Product 1

HCID 545850092-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzenesulfonamideYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of crude tert-butyl {2-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]phenyl}sulfonyl carbamate 1c and 4N HCl in dioxane (3 mL) was stirred at RT for 2 h. The reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was dried and concentrated and the residue was purified by prep. HPLC (Method Y) to provide 2-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzenesulfonamide 1 as a white solid (45 mg, 16% yield). 1H NMR (300 MHz, DMSO) δ 8.05 (m, 1H), 7.63 (m, 3H), 7.39-7.15 (m, 9H), 5.61 (m, 2H), 4.60 (m, 1H), 4.38 (m, 1H), 3.43-3.04 (m, 5H), 2.54 (s, 3H), 2.35-2.17 (m, 4H), 2.13-1.40 (m, 12H). ES-LCMS m/z 612.25 (M+H). Analytical HPLC (Method W) Rt 7.59 (95.89%).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by prep

Sources & evidence

ORD record
ord-4a8e089e079742c4856e461ae7c47da5
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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