Hydrochloric Acid → HCID 136174531, compound

HRID 415565Notes

Reaction equation

HRID 415565 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]3[N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][N:15]3[C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[N:4]=1>O1CCOCC1.CO>[N:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:11]1[N:15]3[CH2:16][CH2:17][NH:18][C:14]3=[N:13][C:12]=1[C:3]([NH2:2])=[N:4]2

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66619871HCID 66619871, compound

Product 1

HCID 136174531HCID 136174531, compoundYield 114.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (3.37 mL of a 4 N solution in 1,4-dioxane) was added to a mixture of tert-butyl 6-amino-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine-8-carboxylate (0.22 g, 0.67 mmol) in methanol (5 mL), and the resulting solution was stirred for three hours. Analysis by HPLC indicated the presence of starting material, and additional hydrogen chloride solution (3 mL) was added. The reaction was stirred at room temperature overnight and concentrated under reduced pressure. The resulting orange solid was triturated with hot acetonitrile and methanol, isolated by filtration, and washed with diethyl ether to provide 173 mg of 9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridin-6-amine as a pale orange solid.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred at room temperature overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting orange solid was triturated with hot acetonitrile and methanol
  5. customisolated by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a3b23760ac2b4c3699829c7b495bed9b
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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