Acetone → HCID 21906464, compound

HRID 1883020Notes

Reaction equation

HRID 1883020 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:25])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:6][CH:7]=1.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:8][C:9](=[O:25])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH:31]([CH3:33])[CH3:30])[CH2:21][CH2:20]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 21906399HCID 21906399, compound

Product 1

HCID 21906464HCID 21906464, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-[(4-piperidinylmethyl)amino]-5-methylbenzamide from Example 204 (1.0 g, 2.78 mmol) in 20 mL of acetone and 6 mL of 95:5 methanol-acetic acid was treated with sodium cyanoborohydride (0.70 g, 11.1 mmol). After stirring at room temperature for 24 h, the reaction mixture was applied to a 10 g SCX column, washed with methanol and eluted with 1 N ammonia in methanol. The yellow fractions were combined and concentrated in vacuo, affording 0.76 g (69%) of the title compound as a yellow solid.

Workup

  1. washwashed with methanol
  2. washeluted with 1 N ammonia in methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d9de0a683424d4d8478e97b3019b2cd
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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