Propyl isocyanate → HCID 11950676, compound

HRID 549253Notes

Reaction equation

HRID 549253 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[NH2:7][C:8]1[C:17]2=[N:18][N:19]([CH2:29][CH3:30])[C:20]([CH2:21][C:22]3([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1>C(Cl)(Cl)Cl>[NH2:7][C:8]1[C:17]2=[N:18][N:19]([CH2:29][CH3:30])[C:20]([CH2:21][C:22]3([OH:28])[CH2:27][CH2:26][N:25]([C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH2:24][CH2:23]3)=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 671577724-[(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]piperidin-4-ol

Product 1

HCID 11950676HCID 11950676, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

n-Propyl isocyanate (86 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 0.277 g of 4-[(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)methyl]-4-hydroxy-N-propylpiperidine-1-carboxamide as a flocculent white solid, mp 208.5-210° 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-450c83a38bb94fb98a997f9e0eb836ff
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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