Acetic Acid → HCID 59730115, compound

HRID 130775Notes

Reaction equation

HRID 130775 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH:8]([C:10]1[CH:25]=[CH:24][C:13]([O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=2)=[CH:12][CH:11]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CO.C(Cl)Cl>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:10]2[CH:25]=[CH:24][C:13]([O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)=[CH:12][CH:11]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 790813-MethylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide2×

Product 1

HCID 59730115HCID 59730115, compoundYield 29.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Using a method similar to Example 345, using 3-methyl-piperidine (0.0420 g, 0.423 mmol), 6-(4-formyl-phenoxy)-nicotinamide (compound of example 332, step 1) (0.101 g, 0.417 mmol), sodium triacetoxyborohydride (0.129 g, 0.610 mmol), and acetic acid (0.035 mL, 0.611 mmol) in 1,2-dichloroethane (8.0 mL) provides, after silica gel chromatography (10:1→7:3 methylene chloride:methanol), 0.0400 g (29%) of the title compound as a white foam: high resolution mass spectrum (electrospray): m/z calc for C19H24N3O2 326.1869, found 326.1841; 1H NMR (DMSO-d6): 8.66 (d, 1H, J=2.2 Hz), 8.29 (dd, 1H, J=2.5, 8.4 Hz), 8.06 (s br, 1H), 7.53 (s br, 1H), 7.38 (d, 2H, J=8.4 Hz), 7.17-7.09 (m, 3H), 3.38-3.28 (m, 2H), 2.83-2.70 (m, 2H), 1.95 (t, 1H, J=10.6 Hz), 1.74-1.41 (m, 5H), 0.97-0.79 (m, 4H).

Workup

  1. customprovides

Sources & evidence

ORD record
ord-61045254dd8f4b24b9422889b8e2e11e
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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