Sodium 2-propanethiolate → HCID 56668008, compound

HRID 1992080Notes

Reaction equation

HRID 1992080 reaction equation
[C:1]([N:3]=[C:4]([N:12]1[CH2:17][CH2:16][C:15]([CH2:24][CH2:25][N:26]2[CH:31]3[CH2:32][CH2:33][CH:27]2[CH2:28][CH:29]([N:34]2[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[N:36]=[C:35]2[CH3:43])[CH2:30]3)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)OC1C=CC=CC=1)#[N:2].[CH3:44][CH:45]([S-:47])[CH3:46].[Na+]>C1COCC1>[C:1]([N:3]=[C:4]([N:12]1[CH2:13][CH2:14][C:15]([CH2:24][CH2:25][N:26]2[CH:31]3[CH2:32][CH2:33][CH:27]2[CH2:28][CH:29]([N:34]2[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[N:36]=[C:35]2[CH3:43])[CH2:30]3)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][CH2:17]1)[S:47][CH:45]([CH3:46])[CH3:44])#[N:2]

Participants

4

Reactant 2

HCID 3470666Sodium 2-propanethiolateHCID 58728442Phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate

Product 1

HCID 56668008HCID 56668008, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate (20 mg, 0.035 mmol) in THF (1 mL) was added sodium 2-propanethiolate (6.8 mg, 0.07 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes before evaporation of the solvent. The crude product was then purified by flash chromatography on silical gel, eluting with a gradient of 0-10% methanol in ethyl acetate to afford isopropyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carbimidothioate as a white solid (14 mg, 72%). 1H NMR (300 MHz, CDCl3) δ 7.69 (d, J=7.5 Hz, 1H), 7.45-7.40 (m, 2H), 7.32-7.24 (m, 4H), 7.21-7.14 (m, 2H), 4.39-4.26 (m, 3H), 3.53 (br, 4H), 2.65 (s, 3H), 2.33-2.05 (m, 4H), 1.99-1.85 (m, 13H), 1.38 (d, J=6.4 Hz, 6H). HRMS m/z (M+H)+ calcd: 555.3270, obsd: 555.3274.

Workup

  1. customThe crude product was then purified by flash chromatography on silical gel
  2. washeluting with a gradient of 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-6b2228681f12426498ad8ef8df78b917
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…