Dimethyl Sulfoxide → HCID 22145797, compound

HRID 1825378Notes

Reaction equation

HRID 1825378 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]1([O:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]=[C:19]([CH:25]([OH:35])[CH2:26][C:27]3[C:32]([Cl:33])=[CH:31][N:30]=[CH:29][C:28]=3[Cl:34])[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl.O>[CH:11]1([O:16][C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]=[C:19]([C:25](=[O:35])[CH2:26][C:27]3[C:28]([Cl:34])=[CH:29][N:30]=[CH:31][C:32]=3[Cl:33])[CH:18]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22145873HCID 22145873, compound

Product 1

HCID 22145797HCID 22145797, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (50 mL) in dry dichloromethane (1.5 mL) is cooled to −30° C. under a nitrogen atmosphere. Dimethyl sulphoxide (80 mL) is added, the mixture stirred for 10 minutes then a solution of (±)-1-(4-cyclopentyloxy-5-methoxypyridin-2-yl)-2-(3,5-dichloropyridin-4-yl)ethanol (210 mg) in dichloromethane (2.5 mL) is added and the mixture stirred for 3 hours. Triethylamine (0.2 mL) is added and the mixture is allowed to warm to room temperature. After pouring into water the organic phase is extracted into dichloromethane, the extracts washed sequentially with 1% aqueous sulphuric acid, water, saturated aqueous sodium bicarbonate and water. The extracts are dried (MgSO4) and evaporated to give a solid. The solid is triturated with pentane, collected and dried to give 1-(4-cyclopentyloxy-5-methoxypyridin-2-yl)-2-(3,5-dichloropyridin-4-yl)ethanone (60 mg), as an off-white solid, m.p. 132° C. [Elemental analysis:—C, 56.80; H, 4.92; N, 7.10% calculated:—C, 56.71; H, 4.78; N, 7.35%].

Workup

  1. stirringthe mixture stirred for 3 hours
  2. extractionis extracted into dichloromethane
  3. washthe extracts washed sequentially with 1% aqueous sulphuric acid, water, saturated aqueous sodium bicarbonate and water
  4. dry with materialThe extracts are dried (MgSO4)
  5. customevaporated
  6. customto give a solid
  7. customThe solid is triturated with pentane
  8. customcollected
  9. customdried

Sources & evidence

ORD record
ord-53e4b63bb61144c888f4b22cc91fb2d9
Source dataset
uspto-grants-2006_05
Patent number
US07045660B2

Reaction notes

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