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 840276Notes

Reaction equation

HRID 840276 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-CH2Cl2 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-4f72723f35f14e02b78a41833040b6a8
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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