3-Chlorobenzenesulphonyl chloride → HCID 58728405, compound

HRID 1992076Notes

Reaction equation

HRID 1992076 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]1[N:17]([CH:18]2[CH2:24][C@H:23]3[N:25]([CH2:26][CH2:27][C:28]4([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[C@H:20]([CH2:21][CH2:22]3)[CH2:19]2)[C:16]2[CH:40]=[CH:41][CH:42]=[CH:43][C:15]=2[N:14]=1>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:31]2[CH2:30][CH2:29][C:28]([CH2:27][CH2:26][N:25]3[C@H:20]4[CH2:21][CH2:22][C@@H:23]3[CH2:24][CH:18]([N:17]3[C:16]5[CH:40]=[CH:41][CH:42]=[CH:43][C:15]=5[N:14]=[C:13]3[CH3:12])[CH2:19]4)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:33][CH2:32]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 10322237HCID 10322237, compound

Product 1

HCID 58728405HCID 58728405, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Chlorobenzenesulfonyl chloride (31.6 mg, 0.122 mmol) was added to a solution of 2-methyl-1-{(1R,5S)-8-[2-(4-phenyl-4-piperidinyl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole (50.0 mg, 0.117 mmol) and diisopropyletheylamine (44.9 mg, 0.348 mmol) in DCM. The reactions were quenched with sat. NaHCO3 and separated with a hydrophobic frit. Flash chromatography on silica 0 to 10% MeOH in EtOAc afforded 1-[(1R,5S)-8-(2-{1-[(3-chlorophenyl)sulfonyl]-4-phenyl-4-piperidinyl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole 14.7 mg (20% yield). MS ES+ 603 (M+H). 1H NMR (300 MHz, chloroform-d) δ ppm 1.6 (m, 2H), 1.7 (m, 4H), 1.9 (m, 8H), 2.4 (m, 4H), 2.6 (s, 3H), 2.8 (m, 2H), 3.4 (m, 2H), 4.6 (m, 1H), 7.2 (m, 5H), 7.3 (m, 3H), 7.4 (t, J=7.9 Hz, 1H), 7.5 (m, 1H), 7.6 (d, J=7.8 Hz, 1H), 7.7 (m, 1H), 7.7 (m, J=1.8, 1.8 Hz, 1H).

Workup

  1. customThe reactions were quenched with sat. NaHCO3
  2. customseparated with a hydrophobic frit

Sources & evidence

ORD record
ord-3a8d646fe5f8478e89c429a9c160e15d
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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