Lawesson's reagent → HCID 86657497, compound

HRID 2359009Notes

Reaction equation

HRID 2359009 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:22][C:11]3([O:16][C:15]4[CH:17]=[CH:18][CH:19]=[N:20][C:14]=4[NH:13][C:12]3=O)[CH2:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:22][C:11]3([O:16][C:15]4[CH:17]=[CH:18][CH:19]=[N:20][C:14]=4[NH:13][C:12]3=[S:32])[CH2:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67393153HCID 67393153, compound

Product 1

HCID 86657497HCID 86657497, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-nitro-5,7-dihydrospiro[cyclopenta[b]pyridine-6,2′-pyrido[3,2-b][1,4]oxazin]-3′(4′H)-one from Step D (450 mg, 1.5 mmol) in toluene (3 mL) is treated with Lawesson's reagent (650 mg, 1.6 mmol) and the mixture heated at reflux for several hours. The solvent is removed in vacuo and the residue is purified by silica gel chromatography (gradient elution with 0-10% MeOH in CH2Cl2) to afford the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for several hours
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by silica gel chromatography (gradient elution with 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1f59245b57de4db3a24c778660ddd652
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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