Hydrochloric Acid → HCID 7174615, compound

HRID 1054318Notes

Reaction equation

HRID 1054318 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([O:13]C)=[O:12])=[CH:8][C:7]([CH3:15])=[N:6][C:5]=2[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.Cl>>[CH3:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]([CH3:15])=[N:6][C:5]=2[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 17025734methyl 3,6-dimethyl-1-phenylpyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 7174615HCID 7174615, compoundYield 81%

Procedure

Synthesized using the procedure for 1 except ester 46 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 (165 mg, 81%) as a light yellow solid. 100% pure by HPLC. 1H NMR (400 MHz, DMSO-d6) δ 13.90 (s, 1H), 8.19 (d, J=7.7 Hz, 2H), 7.56-7.48 (m, 3H), 7.29 (t, J=7.3 Hz, 1H), 2.65 (s, 3H), 2.63 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 167.04, 159.52, 151.67, 142.43, 139.35, 135.32, 129.49, 126.12, 121.13, 118.29, 111.04, 24.92, 16.12. ESI MS: m/z 268.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-fbaebd89cebc4935a66b8e06944e2e76
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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