3-Amino-1-propanol → HCID 59333332, compound

HRID 1893447Notes

Reaction equation

HRID 1893447 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:23]([F:26])([F:25])[F:24])=[CH:5][C:4]=2[N:3]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31]>O1CCOCC1.C(OCC)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:14]2[C:10]3[C:9]4[CH:8]=[CH:7][C:6]([C:23]([F:26])([F:25])[F:24])=[CH:5][C:4]=4[N:3]=[C:2]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])[C:11]=3[N:12]=[CH:13]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 90863-Amino-1-propanol2×HCID 59333318HCID 59333318, compound

Product 1

HCID 59333332HCID 59333332, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloro-1-(4-methoxy-phenyl)-7-trifluoromethyl-1H-imidazo[4,5-c]quinoline (153 mg; 0.41 mmol; 1 eq) in anhydrous 1,4-dioxane (18 mL), 3-aminopropanol (77 μL; 1.0 mmol; 2.5 eq) is added. The resulting solution is heated to reflux and allowed to stir for 19 hours after which period the reaction is still not complete on TLC. Thus, additional 3-aminopropanol (523 μL; 6.9 mmol; 17 eq) is added and the stirring is continued under reflux for 4 hours. The crude mixture is diluted with ethyl acetate (40 mL) and washed three times with a 1M aqueous solution of NaOH (3×40 mL). Aqueous layers are combined and re-extracted with ethyl acetate (75 mL). All organic layers are combined, dried over sodium sulfate and concentrated. The crude residue is purified on silica gel (cyclohexane/ethyl acetate 2:8) to afford the title compound as an off-white powder (145 mg; 0.35 mmol; 85%).

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux
  3. temperatureunder reflux for 4 hours
  4. washwashed three times with a 1M aqueous solution of NaOH (3×40 mL)
  5. extractionre-extracted with ethyl acetate (75 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude residue is purified on silica gel (cyclohexane/ethyl acetate 2:8)

Sources & evidence

ORD record
ord-51962b4f82414514bc460af00481b48d
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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