Acetic Anhydride → 1-acetyl-4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol

HRID 549251Notes

Reaction equation

HRID 549251 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[C:18]2=[N:19][N:20]([CH2:30][CH3:31])[C:21]([CH2:22][C:23]3([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:17]2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1>C(Cl)(Cl)Cl>[C:1]([N:26]1[CH2:27][CH2:28][C:23]([CH2:22][C:21]2[N:20]([CH2:30][CH3:31])[N:19]=[C:18]3[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=[C:9]3[NH2:8])([OH:29])[CH2:24][CH2:25]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 671577724-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol

Product 1

HCID 119506751-acetyl-4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-olYield 61.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetic anhydride (88 μL, 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, the solution was purified via automated flash chromatography eluting with a linear gradient of 2-25% CMA in chloroform. The residue was triturated in acetonitrile and isolated by filtration to provide 0.209 g of 1-acetyl-4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol as a white solid, mp 231-232.5° C.

Workup

  1. customthe solution was purified via automated flash chromatography
  2. washeluting with a linear gradient of 2-25% CMA in chloroform
  3. customThe residue was triturated in acetonitrile
  4. customisolated by filtration

Sources & evidence

ORD record
ord-8db689445ac84cdfaf1b3bd11bbe21c4
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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