Hydrochloric Acid → HCID 16755509, compound

HRID 1986900Notes

Reaction equation

HRID 1986900 reaction equation
C(OC(NC[C@H](F)CC1CCC2CC3CCC=NC=3C3=NN(C(OC(C)(C)C)=O)C(C)C23C1=O)=O)(C)(C)C.[NH2:39][CH2:40][C@H:41]([F:62])[CH2:42][N:43]1[C:52]2[CH:51]=[C:50]3[CH2:53][CH2:54][CH2:55][CH2:56][C:49]3=[CH:48][C:47]=2[C:46]2=[N:57][NH:58][C:59]([CH3:60])=[C:45]2[C:44]1=[O:61].Cl>CO.O1CCOCC1>[NH2:39][CH2:40][C@@H:41]([F:62])[CH2:42][N:43]1[C:52]2[CH:51]=[C:50]3[CH2:53][CH2:54][CH2:55][CH2:56][C:49]3=[CH:48][C:47]=2[C:46]2=[N:57][NH:58][C:59]([CH3:60])=[C:45]2[C:44]1=[O:61].[NH2:39][CH2:40][C@H:41]([F:62])[CH2:42][N:43]1[C:52]2[CH:51]=[C:50]3[CH2:53][CH2:54][CH2:55][CH2:56][C:49]3=[CH:48][C:47]=2[C:46]2=[N:57][NH:58][C:59]([CH3:60])=[C:45]2[C:44]1=[O:61]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 16755509HCID 16755509, compoundHCID 131727497HCID 131727497, compound

Product 2

HCID 16755509HCID 16755509, compoundHCID 16755510HCID 16755510, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To separate solutions of 5-(3-amino-2-(R)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-13) (0.60 g, 1.1 mmol, 1 equiv) and 5-(3-amino-2-(S)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-14) (0.70 g, 13 mmol, 1 equiv) in methanol (20 mL) was added 4 N HCl solution in dioxane (30 mL) and the resulting solutions were stirred at 40° C. for 16 h. The clear gel precipitate was filtered, and the filtered solid was washed with ethyl acetate, dissolved in water and concentrated to yield the hydrochloride salts of 5-(3-amino-2-(R)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-15) and 5-(3-amino-2-(S)-fluoropropyl)-3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-16) as white solids. 1H NMR (500 MHz, CD3OD) δ 7.76 (s, 1H), 7.39 (s, 1H), 5.20 (m, 1H), 4.66 (m, 2H), 3.46 (m, 2H), 2.94 (m, 4H), 2.71 (s, 3H), 1.87 (m, 4H). LRMS m/z (M+H) 329.2 found, 329.2 required.

Workup

  1. filtrationThe clear gel precipitate was filtered
  2. washthe filtered solid was washed with ethyl acetate
  3. dissolutiondissolved in water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-667a39809b174f8796ebcf8d1efa63e6
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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