Dimethylformamide → METHYL[[8-CHLORO-6,11-DIHYDRO-11-[1-[1-OXO-2-(3-PYRIDINYL)ETHYL]-4-PIPERIDINYLIDENE]-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-4-YL]THIO]ACETATE

HRID 1940673Notes

Reaction equation

HRID 1940673 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8](=[C:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:20][CH2:19]3)[C:9]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:10]=3[CH2:11][CH2:12][C:3]=12.[H-].[Na+].[C:35]([O:39][CH3:40])(=[O:38])[CH2:36][SH:37].CN(C=O)C>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:9]2[C:8](=[C:18]3[CH2:19][CH2:20][N:21]([C:24](=[O:32])[CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:22][CH2:23]3)[C:4]3=[N:5][CH:6]=[CH:7][C:2]([S:37][CH2:36][C:35]([O:39][CH3:40])=[O:38])=[C:3]3[CH2:12][CH2:11][C:10]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 226219554-[4,8-Dichloro-5,6-Dihydro-11H-Benzo[5,6]Cyclohepta[1,2-b]Pyridin-11-Ylidene]-1-(3-Pyridinylacetyl)-Piperidine

Product 1

HCID 18715443METHYL[[8-CHLORO-6,11-DIHYDRO-11-[1-[1-OXO-2-(3-PYRIDINYL)ETHYL]-4-PIPERIDINYLIDENE]-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-4-YL]THIO]ACETATEYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the title compound from Example 250 (0.26 grams), sodium hydride (0.08 grams, 60% in mineral oil), methyl thioglycolate (0.19 mL) and anhydrous DMF (15 mL) was stirred while being irradiated with a 200 W lamp for 16 hours. The mixture was diluted with MeOH, concentrated in vacuo, diluted with CH2Cl2 and water, and washed with 1N aqueous NaOH and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo and the residue purified by preparative plate chromatography (silica gel) using 3% MeOH-CH2 Cl2 to afford the title compound (0.05 grams, 15%, MH+ 534).

Workup

  1. customwhile being irradiated with a 200 W lamp for 16 hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with CH2Cl2 and water
  4. washwashed with 1N aqueous NaOH and brine
  5. dry with materialThe organic phase was dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by preparative plate chromatography (silica gel)

Sources & evidence

ORD record
ord-11db828bb86348bb931b8d2dfb136254
Source dataset
uspto-grants-1997_12
Patent number
US05700806

Reaction notes

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