4-Acetylpyridine → HCID 21906434, compound

HRID 988665Notes

Reaction equation

HRID 988665 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1.[C:25]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)(=O)[CH3:26].C([BH3-])#N.[Na+].CO.C(O)(=O)C>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH3:26])[CH2:22][CH2:23]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 142824-AcetylpyridineHCID 5003444Sodium cyanoborohydrideHCID 10129899Acetic acid methanolHCID 21906555HCID 21906555, compound

Product 1

HCID 21906434HCID 21906434, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a small sample of N-(5-chloropyridin-2-yl)-2-(piperidin-4-ylmethylamino)benzamide (0.03 g, 0.1 mmol) weighed out in a 1 mL sealable vial, excess 4-acetylpyridine was added (100 μL, ca. 1 mmol) followed by sodium cyanoborohydride (360 μL of a 1 M solution in tetrahydrofuran) and methanol-acetic acid (95:5). The vial was capped and placed in a shaker at 50° C. for several days until reasonable conversion by TLC was evident. The reaction mixture was then diluted with methanol, shaken well for several minutes, and allowed to stand for 0.5 h before applying it to a 2 g SCX column. After washing well with methanol, the product was gravity-eluted from the column with 2 M ammonia in methanol. The product fractions were combined and concentrated in vacuo to a residue which was triturated in acetonitrile, giving rise to the title compound as a powdery solid (0.03 g, 74%) in >98% purity by HPLC.

Workup

  1. customThe vial was capped
  2. waitplaced in a shaker at 50° C. for several days until reasonable conversion by TLC
  3. washAfter washing well with methanol
  4. washthe product was gravity-eluted from the column with 2 M ammonia in methanol
  5. concentrationconcentrated in vacuo to a residue which
  6. customwas triturated in acetonitrile

Sources & evidence

ORD record
ord-809c571d71a54a88b90901a35d84cec9
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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