Acetic Acid → HCID 57815446, compound

HRID 385578Notes

Reaction equation

HRID 385578 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)=[O:4].[O:14]=[C:15]1[NH:24][C:23]2[N:22]=[C:21]([CH:25]=O)[CH:20]=[CH:19][C:18]=2[CH:17]=[CH:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[F:13][C:2]([F:1])([F:12])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][CH2:25][C:21]2[N:22]=[C:23]3[C:18]([CH:17]=[CH:16][C:15](=[O:14])[NH:24]3)=[CH:19][CH:20]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 450809161-(4-Aminopiperidin-1-yl)-2,2,2-trifluoroethan-1-oneHCID 57815212HCID 57815212, compound

Product 1

HCID 57815446HCID 57815446, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.53 g of 1-(trifluoroacetyl)piperidin-4-amine in 100 mL of dichloromethane, 0.47 g of 7-oxo-7,8-dihydro-1,8-naphthyridine-2-carbaldehyde and 0.16 mL of acetic acid were added, and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was added with 0.86 g of sodium triacetoxyborohydride and stirred at the same temperature for 5 hours. Thereto were added water, a saturated aqueous sodium hydrogen carbonate solution and chloroform, the organic layer was separated, and the aqueous layer was extracted with chloroform. Sodium chloride was further added to the aqueous layer, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=20:1 to obtain 0.59 g of 7-(((1-(trifluoroacetyl)piperidin-4-yl)amino)methyl)-1,8-naphthyridin-2(1H)-one as a light orange foam.

Workup

  1. stirringstirred at the same temperature for 5 hours
  2. customa saturated aqueous sodium hydrogen carbonate solution and chloroform, the organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. additionSodium chloride was further added to the aqueous layer
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-07e8152f1ffb4b05b61d6544cbfc8bc9
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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