Triethylamine → HCID 21906313, compound

HRID 1882956Notes

Reaction equation

HRID 1882956 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[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][NH:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1.Cl.Cl[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH2:22][CH2:23]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 21906555HCID 21906555, compound

Product 1

HCID 21906313HCID 21906313, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A pressure tube was charged with N-(5-chloropyridin-2-yl)-2-(piperidin-4-ylmethylamino)benzamide (100 mg, 0.29 mmol), 4-chloropyridine hydrochloride (87 mg, 0.58 mmol), triethylamine (59 mg, 0.58 mmol), and ethanol (5 mL), sealed, and placed in a 120° C. bath. After 24 h, the mixture was cooled, concentrated, and the residue purified by column chromatography (SiO2: 5 to 10% 2 N ammonia in methanol:methylene chloride) affording 70 mg (57%) of the title compound.

Workup

  1. customsealed
  2. customplaced in a 120° C.
  3. temperaturethe mixture was cooled
  4. concentrationconcentrated
  5. customthe residue purified by column chromatography (SiO2: 5 to 10% 2 N ammonia in methanol:methylene chloride)

Sources & evidence

ORD record
ord-6f553dea0e3c4039902b18e89ba0402d
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

Loading…