Phosphorus oxychloride → HCID 178468964, compound

HRID 2360676Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][NH:13][C:8]=2[N:9]=[C:10](O)[CH:11]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:19])=O.N12CCCN=C1CCCCC2.C([O-])(=O)C.[K+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][NH:13][C:8]=2[N:9]=[C:10]([Cl:19])[CH:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

6-Hydroxy-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (30.0 g), phosphorous oxychloride (12.6 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (22.3 mL) were dissolved in toluene (550 mL) at 0° C. (ice bath), then stirred at 110° C. for 5 h, then cooled to r.t. The mixture was poured into a vigorously stirred solution of potassium acetate (39.9 g) in water (1 l). The aqueous solution was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was used for the next step without further purification. 28.6 g (88%) of the title compound were obtained.

Workup

temperaturecooled to r.t
extractionThe aqueous solution was extracted with ethyl acetate
dry with materialthe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product was used for the next step without further purification

Sources & evidence

ORD record: ord-dc58d8061a5640fd87821ad3e8227667
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686150B2

Reaction notes

Loading…