Lithium borohydride → HCID 22397075, compound

HRID 2187605Notes

Reaction equation

HRID 2187605 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:29])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[CH:10]=2)[N:5]=[C:4]([C:30](OC)=[O:31])[CH:3]=1.[BH4-].[Li+].[Cl-:36].[Na+].O>O1CCCC1.C(OCC)(=O)C>[ClH:36].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:29])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[CH:10]=2)[N:5]=[C:4]([CH2:30][OH:31])[CH:3]=1

Participants

6

Reactant 3

HCID 4148881Lithium borohydrideHCID 22397078HCID 22397078, compoundHCID 57417360Sodium chloride; water

Product 1

HCID 22397075HCID 22397075, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-amino-2-methoxycarbonyl-6-quinolyl)-2-[(4-methylphenoxy)methyl]benzamide (170 mg, 0.385 mmol) obtained in Example 131, Step 5 in tetrahydrofuran (10 ml) was added, by small portions, lithium tetrahydroborate (42 mg, 1.927 mmol) under ice-cooling in an argon stream. After 10 min, the mixture was warmed to room temperature and the mixture was stirred for 2 hr. The reaction mire was diluted with saturated brine and ethyl acetate to separate the layers. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained yellow residue was dissolved in ethyl acetate and 4N hydrochloric acid-dioxane solution (0.5 ml) was added to precipitate hydrochloride. This salt was collected by filtration and dried under reduced pressure at 80° C. to give the title compound (116 mg, 67%, pale-yellow crystals).

Workup

  1. temperaturecooling in an argon stream
  2. customto separate the layers
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained yellow residue was dissolved in ethyl acetate
  7. addition4N hydrochloric acid-dioxane solution (0.5 ml) was added
  8. customto precipitate hydrochloride
  9. filtrationThis salt was collected by filtration
  10. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-a98d94a06841487b844f1ba2c472d1bb
Source dataset
uspto-grants-2002_06
Patent number
US06410561B1

Reaction notes

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