Triethylamine → 3-[(5-chloro-1-isopropyl-1H-benzimidazol-2-yl)thio]-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one

HRID 1453273Notes

Reaction equation

HRID 1453273 reaction equation
Cl[C:2]1[C:3](=[O:25])[O:4][C:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][C:7]=1[OH:8].[Cl:26][C:27]1[CH:39]=[CH:38][C:30]2[N:31]([CH:35]([CH3:37])[CH3:36])[C:32]([SH:34])=[N:33][C:29]=2[CH:28]=1.CCN(CC)CC>>[Cl:26][C:27]1[CH:39]=[CH:38][C:30]2[N:31]([CH:35]([CH3:37])[CH3:36])[C:32]([S:34][C:2]3[C:3](=[O:25])[O:4][C:5]([CH2:14][CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=4)([CH:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:6][C:7]=3[OH:8])=[N:33][C:29]=2[CH:28]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 547203223-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-oneHCID 178456613HCID 178456613, compound

Product 1

HCID 587626653-[(5-chloro-1-isopropyl-1H-benzimidazol-2-yl)thio]-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-oneYield 11.1%

Procedure

A solution of 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one (300 mg, 0.78 mmol), 5-chloro-1-isopropyl-1H-benzimidazole-2-thiol (181 mg, 0.80 mmol) and Et3N (0.1 mL, 0.80 mmol) was stirred at 55° C. for 5 hrs. The mixture was concentrated and purified by prep HPLC to obtain 50 mg product (11% yield). 1H NMR (300 MHz, DMSO-D6) δ: 1.49-1.61 (m, 14H) 2.23-2.30 (m, 2H) 2.57-2.66 (m, 4H) 2.91-2.96 (m, 1H), 3.81 (s, 3H) 4.73-4.79 (m, 1H) 6.93 (d, J=2.07 Hz, 1H), 7.03 (d, J=8.48 Hz, 1H), 7.09 (dd, J=8.57, 2.17 Hz, 1H), 7.12-7.16 (m, 1H), 7.28 (d, J=1.88 Hz, 1H), 7.62 (d, J=8.67 Hz, 1H). ESI-MS calcd for C29H32Cl2N2O4S: 574.1. Found (M+H+): 575.0. Anal. Calcd for C29H32Cl2N2O4S: C, 60.52; H, 5.60; N, 4.87. Found: C, 60.51; H, 5.74; N, 4.58.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep HPLC

Sources & evidence

ORD record
ord-6024e0802b924b819b217520ebfb6d83
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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