Cyclopropyl methyl ketone → HCID 23509778, compound

HRID 988690Notes

Reaction equation

HRID 988690 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-6f616da3dd804fcc9a6b283a25d790c6
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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