Pyridine → HCID 86620600, compound

HRID 1717793Notes

Reaction equation

HRID 1717793 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:40]=[CH:39][C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])=[CH:18][CH:17]=2)=[C:12]([CH3:41])[C:11]=1[OH:42])(=[O:9])[CH3:8].N1C=CC=CC=1.[NH2:49][NH:50][C:51]([NH2:53])=[S:52]>O1CCCC1.CN(C)C=O.CC(C)=O.O>[NH2:49][NH:50][C:51]([NH2:53])=[S:52].[C:7]([C:10]1[CH:40]=[CH:39][C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])=[CH:18][CH:17]=2)=[C:12]([CH3:41])[C:11]=1[OH:42])(=[O:9])[CH3:8]

Participants

8

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 2723789ThiosemicarbazideHCID 66699605HCID 66699605, compound

Product 1

HCID 86620600HCID 86620600, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Add oxalyl chloride (0.660 mg, 5.20 mmol) to a solution of 3-[[4-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid, 1.00 g, 2.04 mmol) in tetrahydrofuran (0.20M). Add dimethylformamide (5 drops). Add pyridine (0.322 g, 4.08 mmol) and thiosemicarbazide (0.223 g, 2.45 mmol). Stir the reaction overnight. Evaporate solvents. Dissolve brown tar in acetone/water. Extract with CH2Cl2 (3×) and ethyl acetate (3×). Combine organic extracts, dry and concentrate to afford the title compound, which was used without further purification (1.20 g, 2.04 mmol, 99%): MS (m/z): 563 (M−H).

Workup

  1. customthe reaction overnight
  2. extractionExtract with CH2Cl2 (3×) and ethyl acetate (3×)
  3. customCombine organic extracts, dry
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-2a1fc2912dbc4371a21cfa9cb0b8f4e0
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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