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 858817Notes

Reaction equation

HRID 858817 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).

Workup

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

Sources & evidence

ORD record
ord-b4f39d57ab42410db58efbabd07ac041
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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