Temozolomide → 3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide

HRID 570921

Reaction equation

HRID 570921 reaction equation
[CH3:1][N:2]1[N:11]=[N:10][C:9]2[N:5]([CH:6]=[N:7][C:8]=2[C:12]([NH2:14])=O)[C:3]1=[O:4].C1C=CC(OC2C=CC(P3(SP(C4C=CC(OC5C=CC=CC=5)=CC=4)(=S)S3)=[S:29])=CC=2)=CC=1>C(Cl)Cl>[CH3:1][N:2]1[C:3](=[O:4])[N:5]2[CH:6]=[N:7][C:8]([C:12](=[S:29])[NH2:14])=[C:9]2[N:10]=[N:11]1

Participants

4

Reactant 2

HCID 5394TemozolomideHCID 118134142,4-Bis(4-phenoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane

Product 1

HCID 33528803-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of temozolomide (3 g, 15.5 mmol) and Belleau's reagent (4.49 g, 8.5 mmol) was refluxed in DCM (80 mL) overnight. The reaction was quenched with water and the precipitate was filtered and washed with diethyl ether to give the pure title compound as an orange solid. (2.75 g, 84%). δH, (DMSO-d6): 9.92 (1H, s), 9.45 (1H, s), 8.81 (1H, s), 3.85 (3H, s).

Workup

  1. customThe reaction was quenched with water
  2. filtrationthe precipitate was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-25cdbd6d9c284c5b9de55719f0c358de
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Linked notes

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