Triethylamine → HCID 11666673, compound

HRID 1823326Notes

Reaction equation

HRID 1823326 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]2[N:12]=[N:13][N:14]=[C:7]2[C:6]=1[NH2:15].C(N(CC)CC)C.[CH2:24]([O:26][CH2:27][C:28](Cl)=[O:29])[CH3:25]>ClCCl>[CH2:24]([O:26][CH2:27][C:28]([NH:15][C:6]1[C:7]2[N:8]([N:12]=[N:13][N:14]=2)[C:9]([CH3:11])=[CH:10][C:5]=1[NH:4][CH2:3][CH:2]([CH3:16])[CH3:1])=[O:29])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 11550312HCID 11550312, compound

Product 1

HCID 11666673HCID 11666673, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of N7-(2-methylpropyl)-5-methyltetraazolo[1,5-a]pyridine-7,8-diamine (8.4 g, 38.1 mmol) in anhydrous dichloromethane (300 mL) was cooled to 0° C. under a nitrogen atmosphere, and triethylamine (5.3 mL, 38.1 mmol) was added. A solution of ethoxyacetyl chloride (4.7 g, 38.1 mmol) in dichloromethane (100 mL) was added dropwise over a period of five minutes, and a homogeneous solution resulted. After the solution was stirred for one hour, it was allowed to warm to room temperature, washed with water (2×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.2 g of 2-ethoxy-N-{7-[(2-methylpropyl)amino]-5-methyltetraazolo[1,5-a]pyridin-8-yl}acetamide as a light tan solid, m.p. 182–185° C.

Workup

  1. customa homogeneous solution resulted
  2. temperatureto warm to room temperature
  3. washwashed with water (2×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f5b8958c44d4af0bfff85750cbb8691
Source dataset
uspto-grants-2006_05
Patent number
US07038053B2

Reaction notes

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