3-Pyridinemethanamine → 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide

HRID 1784006Notes

Reaction equation

HRID 1784006 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.O.C(N=C=NCCCN(C)C)C.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][NH2:50])[CH:44]=1>CN(C=O)C>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:50][CH2:49][C:45]3[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=3)=[O:18])=[CH:19][CH:20]=2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 224003181-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrateHCID 575900854-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid

Product 1

HCID 575899444-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid (0.230 g, 0.69 mmol), 3-hydroxybenzotriazole (0.103 g, 0.76 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrate (0.146 g, 0.76 mmol) in DMF (5 mL) and 3-picolylamine (0.077 mL, 0.76 mmol) is stirred at room temperature for 21 hours. The solvent is removed in vacuo and the residue is triturated with diethyl ether, ethyl acetate and dichloromethane. A pale yellow solid is obtained, washed with water and dried to afford the title compound (241 mg, 82%).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated with diethyl ether, ethyl acetate and dichloromethane
  3. customA pale yellow solid is obtained
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b845953dd7eb40e0a2010114ce8d5640
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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