Triethylamine → HCID 59363295, compound

HRID 446907Notes

Reaction equation

HRID 446907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][C:19]([O-:21])=O)=[N:16][N:17]=3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].CCN=C=NCCCN(C)C.[CH:34]1[CH:35]=C[C:37]2[N:42](O)N=[N:40][C:38]=2[CH:39]=1.CCN(CC)CC.NC1C=NC=CC=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][C:19]([NH:40][C:38]4[CH:37]=[N:42][CH:35]=[CH:34][CH:39]=4)=[O:21])=[N:16][N:17]=3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68701122HCID 68701122, compound

Product 1

HCID 59363295HCID 59363295, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Lithium 2-(6-(3-chlorophenylamino)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)acetate (50 mg, 0.16 mmol) is taken up in DMF (3 ml) and EDCI (45 mg, 0.24 mmol), HOBt (32 mg, 0.24 mmol), Et3N (30 ul, 0.32 mmol), and 3-aminopyridine is added. The reaction mixture is stirred at 60° C. overnight. The reaction mixture is diluted with ethyl acetate, washed with water, and the organic layer concentrated to dryness. Purification by reversed-phase HPLC yields the product, 2-(6-(3-chlorophenylamino)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-N-(pyridin-3-yl)acetamide.

Workup

  1. washwashed with water
  2. concentrationthe organic layer concentrated to dryness
  3. customPurification by reversed-phase HPLC

Sources & evidence

ORD record
ord-4e53127585964ce6a4f8f84cd7f16850
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

Loading…