Tetrahydrofuran → HCID 11649928, compound

HRID 1911759Notes

Reaction equation

HRID 1911759 reaction equation
C[O-].[Na+].O1CCCC1.[CH:9]1([CH2:13][N:14]([CH2:33][CH3:34])[C:15]2[C:24]([CH2:25][NH:26][C:27]3[CH:31]=[C:30]([CH3:32])[O:29][N:28]=3)=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:12][CH2:11][CH2:10]1.[F:35][C:36]([F:50])([F:49])[C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:40]Br>O.C(OCC)(=O)C>[F:35][C:36]([F:49])([F:50])[C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([C:45]([F:48])([F:46])[F:47])[CH:44]=1)[CH2:40][N:26]([CH2:25][C:24]1[C:15]([N:14]([CH2:13][CH:9]2[CH2:12][CH2:11][CH2:10]2)[CH2:33][CH3:34])=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:27]1[CH:31]=[C:30]([CH3:32])[O:29][N:28]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 10942334Sodium MethoxideHCID 57486825HCID 57486825, compound

Product 1

HCID 11649928HCID 11649928, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium methoxide (0.108 g, 2.0 mmol) was added to an anhydrous tetrahydrofuran (6 mL) solution of cyclobutylmethyl-ethyl-{3-[(5-methyl-isoxazol-3-ylamino)-methyl]-quinolin-2-yl}-amine (0.14 g, 0.4 mmol), with stirring, at ambient temperature. After this mixture was stirred for 15 minutes, 3,5-bis-trifluoromethybenzyl bromide (0.08 mL, 0.4 mmol) was added slowly, and stirring was continued overnight. Ethyl acetate (30 mL) and water (30 mL) were added, and the layers were separated. The aqueous layer was back-extracted with ethyl acetate (2×30 mL), and the combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude residue was purified by chromatography on silica gel and eluted with 10-70% hexane in ethyl acetate to afford the title compound (0.045 g, yield: 20%).

Workup

  1. stirringAfter this mixture was stirred for 15 minutes
  2. stirringstirring
  3. customthe layers were separated
  4. extractionThe aqueous layer was back-extracted with ethyl acetate (2×30 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by chromatography on silica gel
  9. washeluted with 10-70% hexane in ethyl acetate

Sources & evidence

ORD record
ord-3cdd4d8d70f147989bd1c173950b755c
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

Loading…