1,1'-Thiocarbonyldiimidazole → HCID 58727697, compound

HRID 1992091Notes

Reaction equation

HRID 1992091 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:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:29]=[CH:30][CH:31]=[CH:32][C:4]=2[N:3]=1.[N:33]1([C:38](N2C=CN=C2)=[S:39])[CH:37]=[CH:36][N:35]=[CH:34]1>C(Cl)Cl>[N:33]1([C:38]([N:20]2[CH2:19][CH2:18][C:17]([CH2:16][CH2:15][N:14]3[C@H:12]4[CH2:11][CH2:10][C@@H:9]3[CH2:8][CH:7]([N:6]3[C:5]5[CH:29]=[CH:30][CH:31]=[CH:32][C:4]=5[N:3]=[C:2]3[CH3:1])[CH2:13]4)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]2)=[S:39])[CH:37]=[CH:36][N:35]=[CH:34]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 587278272-Methyl-1-{8-[2-(4-phenyl-4-piperidinyl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole

Product 1

HCID 58727697HCID 58727697, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methyl-1-{8-[2-(4-phenylpiperidin-4-yl)ethyl]-8-azabicyclo[3.2.1]-oct-3-yl}-1H-benzimidazole (214 mg, 0.5 mmol) in methylene chloride was added 1-(1H-imidazol-1-ylcarbonothioyl)-1H-imidazole (89 mg, 0.5 mmol). The resulting mixture was stirred overnight. After evaporation of the solvents, the crude product was purified by flash chromatography, eluting with a gradient of 0-5% methanol in ethyl acetate, to afford 1-((1R,5S)-8-{2-[1-(1H-imidazol-1-ylcarbonothioyl)-4-phenylpiperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole as a foam (200 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.65 (d, J=7.1 Hz, 1H), 7.42-7.39 (m, 2H), 7.31-7.28 (m, 4H), 7.19-7.10 (m, 3H), 7.07 (s, 1H), 4.62-4.56 (m, 1H), 3.53 (br, 1H), 3.24-3.22 (m, 2H), 2.56 (s, 3H), 2.40-2.32 (m, 4H), 1.99-1.81 (m, 10, H), 1.62 (d, J=7.9 Hz, 2H). HRMS m/z (M+H)+ calcd: 539.2957, obsd: 539.2958.

Workup

  1. customAfter evaporation of the solvents
  2. customthe crude product was purified by flash chromatography
  3. washeluting with a gradient of 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-46b35c9147e043f7bffb74fe418bc1b0
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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