Ammonia → HCID 11952514, compound

HRID 548600Notes

Reaction equation

HRID 548600 reaction equation
Cl[C:2]1[C:11]2=[N:12][N:13]([CH2:25][CH2:26][CH3:27])[C:14]([N:15]([CH2:23][CH3:24])C(=O)OC(C)(C)C)=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:28]>>[CH2:23]([NH:15][C:14]1[N:13]([CH2:25][CH2:26][CH3:27])[N:12]=[C:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:3]=[C:2]2[NH2:28])[CH3:24]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86630218HCID 86630218, compound

Product 1

HCID 11952514HCID 11952514, compound

Procedure

tert-Butyl 4-chloro-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl(ethyl)carbamate (718 mg, 1.85 mmol) and methanolic ammonia (25 mL of a 7 M solution) were heated in a steel Parr vessel in a 150° C. oven for 17 h. The reaction mixture was concentrated, treated with 2 M sodium carbonate and extracted with chloroform. The combined organic layers were dried (magnesium sulfate), filtered, concentrated, and purified by prep HPLC (silica cartridge, eluting with CMA in chloroform). The product was recrystallized from acetonitrile to afford 272 mg of N1-ethyl-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine as white crystals, mp 193-194° C. MS (APCI) m/z 270 (M+1)+; Anal. Calcd for C15H19N5: C, 66.89; H, 7.11; N, 26.00. Found: C, 66.65; H, 7.20; N, 26.19.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with 2 M sodium carbonate
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by prep HPLC (silica cartridge, eluting with CMA in chloroform)
  8. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-87a0391157084921834360693a2f735a
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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