Water → HCID 23438723, compound

HRID 2120170Notes

Reaction equation

HRID 2120170 reaction equation
C(O[C:6]([N:8]1CCC(C=O)CC1)=O)(C)(C)C.N[C:17]1[C:18]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])=[N:19][CH:20]=[CH:21][CH:22]=1.[C:33]1([CH3:43])C=CC(S([O-])(=O)=O)=C[CH:34]=1.[NH+:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.O>C1C=CC=CC=1>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:23]([C:18]2([NH:8][CH2:6][CH:47]3[CH2:48][CH2:49][N:44]([CH:33]([CH3:43])[CH3:34])[CH2:45][CH2:46]3)[CH:17]=[CH:22][CH:21]=[CH:20][NH:19]2)=[O:24])=[N:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 115578513-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

Product 1

HCID 23438723HCID 23438723, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 1-tert-butoxycarbonylpiperidine-4-carboxaldehyde (2.00 g, 9.38 mmol), 3-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (2.33 g, 9.38 mmol), and pyridinium p-toluenesulfonate (236 mg, 0.94 mmol) in benzene (100 mL) was heated at reflux with azeotropic removal of water. After 48 h, the mixture was concentrated and the residue was purified by column chromatography (SiO2: methylene chloride) yielding the title compound, which was contaminated with 3-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide and was used without further purification.

Workup

  1. temperaturewas heated
  2. concentrationthe mixture was concentrated
  3. customthe residue was purified by column chromatography (SiO2: methylene chloride)

Sources & evidence

ORD record
ord-59d8d17dccc74d308602deb6a853b289
Source dataset
uspto-grants-2004_02
Patent number
US06689780B1

Reaction notes

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