6-Hydroxypyridazine-3-carboxylic Acid → 1,4,5,6-Tetrahydro-6-oxo-3-pyridazinecarboxylic acid

HRID 927189

Reaction equation

HRID 927189 reaction equation
[2H][C@@:2]([C:11]([OH:13])=[O:12])([CH:4]([2H])[CH:5]([2H])[C:6](=[O:8])[NH2:7])[NH2:3].C(C1C=CC(=O)NN=1)(O)=O>>[C:11]([C:2]1[CH2:4][CH2:5][C:6](=[O:8])[NH:7][N:3]=1)([OH:13])=[O:12]

Participants

3

Reactant 2

HCID 3059706-Hydroxypyridazine-3-carboxylic AcidHCID 86671832HCID 86671832, compound

Product 1

HCID 996211,4,5,6-Tetrahydro-6-oxo-3-pyridazinecarboxylic acid

Procedure

A number of deuterated glutamines (starting material for preparing Compound B) have previously been made, including 2,3,4-trideutero-glutamine (i.e., R2=D, R4=D, and Z=D), which was made via the deuterium reduction of 6-carboxy-3(2H)-pyridazone (see Stogniew, J. Labelled Compounds and Radiopharmaceuticals 1981, 18(6), 897-903), and 2,2,3,3,4 pentadeutero-glutamine (i.e., R2-R5=D and Z=D), which was obtained in a multi-step synthesis (see Blomquist, J. Org. Chem. 1966, 12, 4121-27). Stogniew also notes that the 5-mono-deutero-glutamine could be obtained through deuterium reduction of 4,5-dihydro-6-carboxy-3(2H)-pyridazone.

Workup

  1. customwhich was obtained in a multi-step synthesis (see Blomquist, J. Org. Chem. 1966, 12, 4121-27)

Sources & evidence

ORD record
ord-632db36a8d534b8ebe1258eaf1cf765a
Source dataset
uspto-grants-2016_03
Patent number
US09290475B2

Linked notes

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