Ethanol hydrochloride → HCID 136174528, compound

HRID 415550Notes

Reaction equation

HRID 415550 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[N:17](C(OC(C)(C)C)=O)[CH2:16][C@H:15]([CH3:25])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.CCO>C(Cl)(Cl)Cl>[CH3:25][C@@H:15]1[N:14]2[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[NH:17][CH2:16]1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 66619826HCID 66619826, compound

Product 1

HCID 136174528HCID 136174528, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl (10S)-6-amino-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate (130 mg, 0.383 mmol) was treated with 10 mL of 3.0 M HCl/EtOH and heated up to reflux for about 20 minutes. The volatiles were then removed under reduced pressure, and the resulting residue was partitioned between CH2Cl2 and H2O. The layers were separated, and the aqueous one was extracted again with CH2Cl2, and the combined organic layers were discarded. The aqueous layer was then treated with concentrated ammonium hydroxide solution until the pH ˜11. The layer was extracted with CH2Cl2 (3×). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give a white solid. Chromatography (SiO2, 20-40% CMA/CHCl3) afforded (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (55 mg) as an off white solid, m.p. 265-273° C.

Workup

  1. temperatureheated up
  2. temperatureto reflux for about 20 minutes
  3. customThe volatiles were then removed under reduced pressure
  4. customthe resulting residue was partitioned between CH2Cl2 and H2O
  5. customThe layers were separated
  6. extractionthe aqueous one was extracted again with CH2Cl2
  7. additionThe aqueous layer was then treated with concentrated ammonium hydroxide solution until the pH ˜11
  8. extractionThe layer was extracted with CH2Cl2 (3×)
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give a white solid

Sources & evidence

ORD record
ord-32c2fbdd16a64f3eb6dd055bedab831e
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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