Potassium Carbonate → di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate

HRID 2283803Notes

Reaction equation

HRID 2283803 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[N:16]([CH2:43][CH2:44][CH3:45])[N:17]=[C:18]2[C:27]=1[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:20]=[C:19]2[N:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=O)C>CO>[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[N:16]([CH2:43][CH2:44][CH3:45])[N:17]=[C:18]2[C:27]=1[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:20]=[C:19]2[N:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 669589344-{4-[bis(tert-butoxycarbonyl)amino]-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl}butyl acetate

Product 1

HCID 66958564di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonateYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (6 mg, 0.041 mmol) was added to a solution of 4-{4-[bis(tert-butoxycarbonyl)amino]-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl}butyl acetate (0.8823 g, 1.632 mmol) in methanol (5 mL). The mixture was stirred at ambient temperature for 1.3 hours. The volatiles were removed under reduced pressure. The resulting oil was purified by flash chromatography (silica gel, eluted with 100% ethyl acetate) to yield 0.1466 g of di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate in about 87% purity.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe resulting oil was purified by flash chromatography (silica gel, eluted with 100% ethyl acetate)

Sources & evidence

ORD record
ord-3cbf8788fb4b4b83b8935737e3b6915b
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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