Ammonia → HCID 86630221, compound

HRID 548601Notes

Reaction equation

HRID 548601 reaction equation
C(OC([N:8]([C:24]1[N:25]([CH2:38][CH2:39][CH3:40])[N:26]=[C:27]2[C:36]=1[C:35]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:29]=[C:28]2[Cl:37])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)=O)(C)(C)C.[ClH:41].[NH3:42]>CO.C(O)C>[ClH:37].[ClH:41].[NH:14]1[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][NH:8][C:24]2[N:25]([CH2:38][CH2:39][CH3:40])[N:26]=[C:27]3[C:36]=2[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N:29]=[C:28]3[NH2:42])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86630220HCID 86630220, compound

Product 1

HCID 86630221HCID 86630221, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A solution of tert-butyl 4-{2-[(tert-butoxycarbonyl)(4-chloro-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)amino]ethyl}piperidine-1-carboxylate (1.41 g) in 7N ammonia in methanol (25 mL) was placed in a stainless steel pressure vessel and heated at 150° C. for 18 hours. The reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure to provide a brown residue. The residue was suspended in anhydrous ethanol (20 mL). Hydrochloric acid (4 mL of 3M) was added and the reaction mixture was heated at reflux for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was triturated with diethyl ether and the resulting solid was isolated by filtration to provide 0.7 g of N1-(2-piperidin-4-ylethyl)-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine dihydrochloride as a brown solid. MS (APCI) m/z 353.30 (M+H)+. The experiment was repeated using 5.75 g of tert-butyl 4-{2-[(tert-butoxycarbonyl)(4-chloro-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)amino]ethyl}piperidine-1-carboxylate in 70 mL of 7N ammonia in methanol followed by treatment with 16.75 mL of 3M hydrochloric acid to provide 4.1 g of product as a brown solid. MS (APCI) m/z 353.26 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customto provide a brown residue
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 4 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. customthe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-1c5060eb6ba64700bc38be6cac54d208
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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