Cyclopropyl methyl ketone → HCID 23509778, compound

HRID 1883021Notes

Reaction equation

HRID 1883021 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.[CH:26]1([C:29]([CH3:31])=O)[CH2:28][CH2:27]1.C([BH3-])#N.[Na+]>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:29]([CH:26]3[CH2:28][CH2:27]3)[CH3:31])[CH2:21][CH2:20]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 5003444Sodium cyanoborohydrideHCID 21906399HCID 21906399, compound

Product 1

HCID 23509778HCID 23509778, compoundYield 64%

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 6 mL of 95:5 methanol-acetic acid was treated with excess cyclopropylmethyl ketone (5.52 mL, 55.6 mmol), followed by sodium cyanoborohydride (0.65 g, 10.3 mmol). After stirring at room temperature for 24 hr, the reaction mixture was concentrated in vacuo; and the residue was subjected to silica gel chromatography. Elution with 9:1 dichloromethane-methanol afforded 0.76 g (64%) of the title compound as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washElution with 9:1 dichloromethane-methanol

Sources & evidence

ORD record
ord-b192ed6408c6473595bfd870aea23728
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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