Acetone → HCID 21906395, compound

HRID 1883024Notes

Reaction equation

HRID 1883024 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1)=[O:8].C([BH3-])#N.[Na+].[CH3:30][C:31]([CH3:33])=O>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([CH:31]([CH3:33])[CH3:30])[CH2:24][CH2:25]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 21906582HCID 21906582, compound

Product 1

HCID 21906395HCID 21906395, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-chloro-N-(5-fluoropyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide from Example 218 (0.50 g, 1.37 mmol) in 10 mL of acetone and 6 mL of 95:5 methanol-acetic acid was treated with sodium cyanoborohydride (0.35 g, 5.5 mmol). After stirring at 50° C. for 24 h, the solution was concentrated in vacuo; and the residue was subjected to silica gel chromatography. Elution with 98:2 dichloromethane-methanol furnished the title compound (0.12 g, 21%) as a yellow solid.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. washElution with 98:2 dichloromethane-methanol

Sources & evidence

ORD record
ord-c1b5a379fc1240ce85ef72a2775d03c9
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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