Triethylamine → HCID 178513371, compound

HRID 1882997Notes

Reaction equation

HRID 1882997 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-d20829ebc6964e548210bd386bc1f1f8
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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