Acetic Acid → 2-amino-5H-thiazolo[4,5-d]pyridazin-4-one

HRID 908640Notes

Reaction equation

HRID 908640 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:12])[S:8][C:9]=1[CH:10]=O)=O.O.[NH2:14][NH2:15].C(O)(=O)C>C(O)C.CO>[NH2:12][C:7]1[S:8][C:9]2[CH:10]=[N:15][NH:14][C:3](=[O:2])[C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 597038102-Amino-5-formyl-thiazole-4-carboxylic acid methyl ester

Product 1

HCID 597038212-amino-5H-thiazolo[4,5-d]pyridazin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The compound (788 mg) obtained in Step 3 was suspended in ethanol (7.8 ml), and hydrazine monohydrate (243 μl) and acetic acid (780 μl) were added, with stirring at room temperature. The mixture was stirred overnight at a bath temperature of 100° C. and returned to room temperature. The reaction mixture was concentrated under reduced pressure, and the obtained crude crystals were suspended in methanol, collected by filtration and dried to give the title compound (690 mg).

Workup

  1. stirringThe mixture was stirred overnight at a bath temperature of 100° C.
  2. customreturned to room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe obtained crude crystals
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-bcd1f9042c274c25acf7c5d3c3ea2b96
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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