Sodium Carbonate → HCID 57750720, compound

HRID 549252Notes

Reaction equation

HRID 549252 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[NH2:10][C:11]1[C:20]2=[N:21][N:22]([CH2:32][CH3:33])[C:23]([CH2:24][C:25]3([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[C:19]2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:10][C:11]1[C:20]2=[N:21][N:22]([CH2:32][CH3:33])[C:23]([CH2:24][C:25]3([OH:31])[CH2:30][CH2:29][N:28]([S:2]([CH3:1])(=[O:5])=[O:3])[CH2:27][CH2:26]3)=[C:19]2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81560Methanesulfonic anhydrideHCID 671577724-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol

Product 1

HCID 57750720HCID 57750720, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonic anhydride (0.160 g, 0.922 mmol) was added to a slurry of 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol (0.300 g, 0.922 mmol) in chloroform (10 mL). After 16 hours, 2M aqueous sodium carbonate was added and the biphasic mixture was stirred for 30 minutes resulting in a white precipitate. The mixture was extracted with 10% methanol in dichloromethane. The solution was concentrated. The residue was purified via automated flash chromatography and recrystallized from acetonitrile to provide 0.165 g of 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]-1-(methylsulfonyl)piperidin-4-ol as a white solid, mp 268-270° C.

Workup

  1. customresulting in a white precipitate
  2. extractionThe mixture was extracted with 10% methanol in dichloromethane
  3. concentrationThe solution was concentrated
  4. customThe residue was purified via automated flash chromatography
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-9556807ff6134ed087fe0478d50ff609
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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