Hydrochloric Acid → 6-(2-FURYL)-1,3-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-4-CARBOXYLIC ACID

HRID 1054317Notes

Reaction equation

HRID 1054317 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([C:17]([O:19]C)=[O:18])[C:9]2[C:14]([CH3:15])=[N:13][N:12]([CH3:16])[C:10]=2[N:11]=1.Cl>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([C:17]([OH:19])=[O:18])[C:9]2[C:14]([CH3:15])=[N:13][N:12]([CH3:16])[C:10]=2[N:11]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 17025901HCID 17025901, compound

Product 1

HCID 162277156-(2-FURYL)-1,3-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-4-CARBOXYLIC ACIDYield 79%

Procedure

Synthesized using the procedure for 1 except ester 37 was used as the starting material. After the work up and acidifying the aqueous layer with 1N HCl, solid precipitated which was filtered off and dried on high vacuum to provide the title compound (203 mg, 79%) as a beige solid. 100% pure by HPLC. 1H NMR (400 MHz, DMSO-d6) δ 13.91 (s, 1H), 7.91 (s, 1H), 7.85 (s, 1H), 7.33 (d, J=2.9 Hz, 1H), 6.72-6.67 (m, 1H), 3.98 (s, 3H), 2.55 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 166.91, 152.73, 152.00, 147.61, 145.67, 140.08, 135.59, 113.13, 112.56, 111.40, 109.74, 33.82, 15.92. ESI MS: m/z 258.0 (M+H)+.

Workup

  1. customSynthesized
  2. customprecipitated which
  3. filtrationwas filtered off
  4. customdried on high vacuum

Sources & evidence

ORD record
ord-61d142c5cfa34e94a4ea68f57b21257a
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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