Triethylamine → HCID 178519101, compound

HRID 858798Notes

Reaction equation

HRID 858798 reaction equation
Cl[C:2]1[C:3](=[O:22])[O:4][C:5]([CH2:14][CH2:15][C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=2)([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][C:7]=1[OH:8].[N:23]1[CH:28]=[CH:27][C:26]([C:29]2[NH:30][C:31]([SH:34])=[N:32][N:33]=2)=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C=O)C>[C:16]1([CH2:15][CH2:14][C:5]2([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[O:4][C:3](=[O:22])[C:2]([S:34][C:31]3[NH:30][C:29]([C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)=[N:33][N:32]=3)=[C:7]([OH:8])[CH2:6]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 575272693-Chloro-6-(2-cyclohex-1-enyl-ethyl)6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-oneHCID 1785279605-pyridin-4-yl-1H-1,2,4-triazole-3-thiol

Product 1

HCID 178519101HCID 178519101, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 3-Chloro-6-(2-cyclohex-1-enyl-ethyl)-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one (150 mg, 0.46 mmol, from Step 1 below), 5-Pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (82 mg, 0.46 mmol), and triethylamine (64 □L, 0.46 mmol) dissolved in DMF (5 mL) was heated to 55° C. under N2 for 8 h. The resulting mixture was concentrated and purified by Prep HPLC to give the title compound (58 mg, 27%) as a pale yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-f285b83780054a808b00b28bf142e322
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…