Acetic Acid → HCID 9846565, compound

HRID 988602Notes

Reaction equation

HRID 988602 reaction equation
FC(F)(F)C(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.[N:33]1[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO.C(O)(=O)C.CO>[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]([CH2:39][C:36]3[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=3)[CH2:28][CH2:27]2)=[O:25])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21906487HCID 21906487, compound

Product 1

HCID 9846565HCID 9846565, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of N-(5-chloropyridin-2-yl)-2-[(piperidin-4-ylcarbonyl)amino]benzamide trifluoroacetate (25 mg, 0.053 mmol) in methanol (0.5 mL) was added 4-pyridinecarboxaldehyde (17.1 mg, 0.16 mmol) followed by a solution of sodium cyanoborohydride (7 mg, 0.106 mmol) in 7.5% acetic acid/methanol (1 mL). After shaking for 15 h, the solution was loaded onto an SCX column, which was pretreated with a solution of 5% acetic acid in methanol. The column was washed once with methanol and eluted with 2 N ammonia in methanol. The product containing fractions were combined and concentrated in vacuo. The residue was dissolved in a small amount of methanol and a few drops of acetic anhydride were added. After shaking for 0.5 h, the SCX purification procedure was repeated to give 9.8 mg (41%, 91% pure by HPLC analysis) of the title compound.

Workup

  1. washThe column was washed once with methanol
  2. washeluted with 2 N ammonia in methanol
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in a small amount of methanol and a few drops of acetic anhydride
  6. additionwere added
  7. stirringAfter shaking for 0.5 h
  8. customthe SCX purification procedure

Sources & evidence

ORD record
ord-6cf31feefabc47daabc83f63d9c3fdb9
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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