Sodium Hydroxide → HCID 58083318, compound

HRID 390376Notes

Reaction equation

HRID 390376 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=1)[C:7]=2[CH3:29])=O.[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CN1CCCC1=O.C(O)(=O)C>[OH:37][C@H:32]1[CH2:33][CH2:34][CH2:35][CH2:36][C@@H:31]1[NH:30][CH2:1][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH:13][C:14](=[O:28])[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:19][CH:20]=1)[C:7]=2[CH3:29]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 735777(1R,2R)-2-AminocyclohexanolHCID 5049666Sodium triacetoxyborohydrideHCID 86661906HCID 86661906, compound

Product 1

HCID 58083318HCID 58083318, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(3-Formyl-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide (1.0 g) obtained in Reference Example 2% and trans-2-aminocyclohexanol (546 mg) were suspended in 1-methyl-2-pyrrolidone (20 mL) and acetic acid (7.0 mL) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (2.35 g) was added and the mixture was stirred at room temperature for 3 hr. 1N Aqueous sodium hydroxide solution was added to quench the reaction and basify the mixture. The mixture was partitioned and extracted with ethyl acetate, the organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL), and the mixture was washed with ethyl acetate. 1N Aqueous sodium hydroxide solution was added to the aqueous layer, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was recrystallized from ethyl acetate-diisopropyl ether to give the title compound (395 mg, yield 32%) as a colorless solid.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe mixture was partitioned
  4. extractionextracted with ethyl acetate
  5. additionthe organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL)
  6. washthe mixture was washed with ethyl acetate
  7. addition1N Aqueous sodium hydroxide solution was added to the aqueous layer
  8. customthe mixture was partitioned
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe obtained solid was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-c9526934bc554a689b4efdcc4a7928a3
Source dataset
uspto-grants-2013_02
Patent number
US08383647B2

Reaction notes

Loading…