Acetic Acid → HCID 21906201, compound

HRID 988605Notes

Reaction equation

HRID 988605 reaction equation
F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[N:13][CH:14]=1.[C:33](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>CC(C)=O.ClCCCl>[ClH:8].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH:2]([CH3:3])[CH3:33])[CH2:28][CH2:27]2)=[O:25])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 21906487HCID 21906487, compound

Product 1

HCID 21906201HCID 21906201, compoundYield 114.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 180AcetoneSolvent

Procedure

To a stirred suspension of N-(5-chloropyridin-2-yl)-2-[(piperidin-4-ylcarbonyl)amino]benzamide trifluoroacetate (0.4 g, 0.85 mmol) in acetone (6 mL) and 1,2-dichloroethane (10 mL) was added glacial acetic acid (0.2 mL, 3.84 mmol) followed by then sodium triacetoxyborohydride (0.81 g, 3.84 mmol). After stirring for 15 h, saturated aqueous ammonium chloride (10 mL) was added. After stirring for 0.5 h, the mixture was partitioned between dichloromethane and water and the layers separated. The organic phase was washed with saturated aqueous sodium chloride, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was then purified by preparative RPHPLC (C18), eluting with a linear gradient of 90/10 to 60/40 (0.01% HCl/acetonitrile) over 180 min. The product containing fractions were combined and lyophilized to give 0.212 g (57%) of the title compound as a white solid.

Workup

  1. stirringAfter stirring for 0.5 h
  2. customthe mixture was partitioned between dichloromethane and water
  3. customthe layers separated
  4. washThe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by preparative RPHPLC (C18)
  9. washeluting with a linear gradient of 90/10 to 60/40 (0.01% HCl/acetonitrile) over 180 min
  10. additionThe product containing fractions

Sources & evidence

ORD record
ord-55689c4235544b39b0848a549bb95d33
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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