Acetic Acid → HCID 9954796, compound

HRID 2120169Notes

Reaction equation

HRID 2120169 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]2[C:23]([NH:24][C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[N:13][CH:14]=1.[CH3:33][C:34]([CH3:36])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO>[ClH:8].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]2[C:23]([NH:24][C:25]([CH:27]3[CH2:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:33])[CH2:31][CH2:32]3)=[O:26])=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 23438727HCID 23438727, compound

Product 1

HCID 9954796HCID 9954796, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a stirring suspension of N-(5-chloropyridin-2-yl)-3-[(piperidin-4-ylcarbonyl)amino]pyridine-2-carboxamide trifluoroacetate (0.34 g, 0.72 mmol) in 1,2-dichloroethane (10 mL) was added acetone (10 mL), followed by acetic acid (0.7 mL, 2.88 mmol) and then sodium triacetoxyborohydride (0.61 g, 2.88 mmol). After stirring overnight, the solution was loaded onto an SCX column (prewashed with 5% acetic acid in methanol) and washed with methanol. The product was then eluted from the column with a 2 N solution of ammonia in methanol. The product containing fractions were concentrated in vacuo and the compound was purified by preparative RPHPLC (C18), eluting with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min, to give 0.14 g (44%) of a white solid.

Workup

  1. washwashed with methanol
  2. washThe product was then eluted from the column with a 2 N solution of ammonia in methanol
  3. additionThe product containing fractions
  4. concentrationwere concentrated in vacuo
  5. customthe compound was purified by preparative RPHPLC (C18)
  6. washeluting with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min

Sources & evidence

ORD record
ord-735a3e47ee5b40e98129406e3cf91fe6
Source dataset
uspto-grants-2004_02
Patent number
US06689780B1

Reaction notes

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