Triethylamine → HCID 178513371, compound

HRID 1247096Notes

Reaction equation

HRID 1247096 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:32])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3C#N)[CH2:20][CH2:19]2)=[N:6][CH:7]=1.C([N:35]([CH2:38]C)CC)C.Cl.[NH2:41][OH:42]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:32])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([C:38](=[NH:35])[NH:41][OH:42])[CH:25]=3)[CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21906631HCID 21906631, compound

Product 1

HCID 178513371HCID 178513371, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-[1-(3-cyanopyridin-4-yl)piperidin-4-ylmethylamino]benzamide (50 mg, 0.11 mmol) and triethylamine (22 mg, 0.22 mmol) in ethanol (5 mL) was treated with hydroxylamine hydrochloride (12 mg, 0.17 mmol). After 16 h, the mixture was concentrated and the residue was purified by column chromatography (SiO2; 5% methanol in methylene chloride) yielding 40 mg (75%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by column chromatography (SiO2; 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-6693a8da56fc481a9f4dddccb9e7a196
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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