Hydrochloric Acid → HCID 67434271, compound

HRID 1803391Notes

Reaction equation

HRID 1803391 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][N:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:16][C@H:15]([CH2:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[ClH:34]>C(O)C>[OH2:20].[ClH:34].[ClH:34].[NH2:26][CH2:25][CH2:24][CH2:23][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[CH2:18][N:17]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67434799HCID 67434799, compound

Product 1

HCID 67434271HCID 67434271, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
75 °C

Procedure

tert-Butyl 3-[(11S)-6-amino-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (5.41 g, 11.4 mmol) was dissolved in 25 mL of ethanol and 25 mL of a 1.8 M solution of HCl in ethanol was added. The reaction mixture was heated to 75° C. After 1 hour, the reaction mixture was cooled and filtered to give a white solid. The resulting solid was stirred in refluxing ethanol for 30 minutes. The suspension was cooled and filtered to give a white solid. The solid was washed with a small portion of cold ethanol and then dried by suction to give (11S)-11-(3-aminopropyl)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine dihydrochloride hydrate (2.98 g) as an off-white powder (Anal. calcd for C17H22N6O2S2.2.0 HCl.1.0H2O: C, 43.87; H, 5.63; N, 18.06. Found: C, 43.83; H, 5.53; N, 17.99). The free base could be prepared by dissolving the material in dilute NH4OH solution and extraction into CHCl3.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationfiltered
  3. customto give a white solid
  4. temperatureThe suspension was cooled
  5. filtrationfiltered
  6. customto give a white solid
  7. washThe solid was washed with a small portion of cold ethanol
  8. customdried by suction

Sources & evidence

ORD record
ord-9b9d539927c74fa98b5d58b46ec6a184
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

Loading…