Hydrochloric Acid → HCID 68350731, compound

HRID 1909237Notes

Reaction equation

HRID 1909237 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:16]2[CH:28]=[N:27][N:26]([CH:29]([CH3:31])[CH3:30])[C:17]=2[N:18]=[C:19]([C:21]([O:23]CC)=[CH2:22])[CH:20]=1)=[O:14].C([O-])(O)=O.[Na+]>CO.C(Cl)Cl>[C:21]([C:19]1[CH:20]=[C:15]([C:13]([NH:12][CH2:11][C:4]2[C:5](=[O:10])[NH:6][C:7]([CH3:9])=[CH:8][C:3]=2[CH3:2])=[O:14])[C:16]2[CH:28]=[N:27][N:26]([CH:29]([CH3:30])[CH3:31])[C:17]=2[N:18]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68351225HCID 68351225, compound

Product 1

HCID 68350731HCID 68350731, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

35% HCl (4 mL) was added to the N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(1-ethoxyvinyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.12 g, 0.293 mmol) at 0° C. and stirred it at room temperature for 1 h. After completion of reaction, saturated NaHCO3 solution was added to it and extraction was carried out by using 5% MeOH/DCM, the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the desired compound (90% yield). LCMS: 382.10 (M+1)+; HPLC: 99.55% (@ 254 nm) (Rt;6.316); 1H NMR (DMSO-d6, 400 MHz) δ 11.55 (s, 1H), 9.09 (bs, 1H), 8.48 (s, 1H), 8.14 (s, 1H), 5.89 (s, 1H), 5.35-5.29 (m, 1H), 4.36 (d, 2H, J=4.0 Hz), 2.75 (s, 3H), 2.21 (s, 3H), 2.12 (s, 3H), 1.56 (d, 6H, J=6.8 Hz).

Workup

  1. additionwas added to it and extraction
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f6f98d3ae264bde9a19fdfa687b70e9
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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