Cyclopropylamine → 7-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid cyclopropylamide

HRID 2112936Notes

Reaction equation

HRID 2112936 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C[Al](C)C.C([O:11][C:12]([C:14]1[N:19]2[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH3:28])=[O:25])[N:22]=[C:18]2[CH:17]=[C:16]([Br:29])[CH:15]=1)=O)C>O1CCCC1.CCCCCCC.ClCCl>[CH:1]1([NH:4][C:12]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH3:28])=[O:25])[N:22]=[C:18]3[CH:17]=[C:16]([Br:29])[CH:15]=2)=[O:11])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 69828CyclopropylamineHCID 16682925TrimethylaluminumHCID 576430687-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 688398247-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid cyclopropylamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

Cyclopropylamine (0.136 g, 2.38 mmol) was suspended in tetrahydrofuran (2.00 mL) and cooled in an ice bath. This solution was charged with 2 molar trimethylaluminum in heptane (0.300 mL). After 20 minutes the solution was charged with 7-bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester produced as in Example 6, (0.248 g, 0.696 mmol) and shaken. After 24 hours the reaction was dissolved in dichloromethane and washed with saturated aqueous ammonium chloride. The organic layers were dried over magnesium sulfate and concentrated to afford 7-bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid cyclopropylamide MS (ACPI+): m/z 368.2 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. customproduced as in Example 6, (0.248 g, 0.696 mmol)
  3. washwashed with saturated aqueous ammonium chloride
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b2b893e5afb452e80bdb78d4f1edd3b
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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