Hexylamine → HCID 44466084, compound

HRID 415493Notes

Reaction equation

HRID 415493 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:17](=[O:18])[N:9]2[CH:10]=[C:11]([C:14](O)=[O:15])[CH:12]=[CH:13][C:8]2=[N:7]1.[CH:23]1[CH:24]=[CH:25][C:26]2N(O)N=[N:29][C:27]=2[CH:28]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.C(N)CCCCC>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:17](=[O:18])[N:9]2[CH:10]=[C:11]([C:14]([NH:29][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:28])=[O:15])[CH:12]=[CH:13][C:8]2=[N:7]1

Participants

7

Reactant 5

HCID 8102HexylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44466336HCID 44466336, compound

Product 1

HCID 44466084HCID 44466084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 15-mL round-bottom flask 2-(3,4-dichlorobenzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (0.065 mmol) was dissolved in dichloromethane (2.4 mL). HOBT (0.01 mmol), EDC hydrochloride (0.13 mmol), triethylamine (0.13 mmol), and n-hexylamine (0.13 mmol) were added sequentially to the reaction flask and stirred overnight. Extracted with 1N aqueous HCl and dichloromethane. Organic layer concentrated and residue chromatographed on silica gel using 2% MeOH in dichloromethane as eluent. Product 2-(3,4-dichlorobenzyl)-3-oxo-N-hexyl-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide was obtained as white solid.

Workup

  1. extractionExtracted with 1N aqueous HCl and dichloromethane
  2. concentrationOrganic layer concentrated
  3. customresidue chromatographed on silica gel using 2% MeOH in dichloromethane as eluent

Sources & evidence

ORD record
ord-77546d4d0ed84a87bbce904e501b5e95
Source dataset
uspto-grants-2012_01
Patent number
US08088792B2

Reaction notes

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