Ethyl Acetate → HCID 15547190, compound

HRID 1375424Notes

Reaction equation

HRID 1375424 reaction equation
[H-].[Na+].[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[CH:11]1([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][N:22]=3)[C:17]([C:24](Cl)=[O:25])=[CH:16]2)[CH2:13][CH2:12]1.C(OCC)(=O)C>C1COCC1.O>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][C:24]([C:17]2[C:18]3[C:23](=[N:22][CH:21]=[CH:20][CH:19]=3)[N:15]([CH2:14][CH:11]3[CH2:13][CH2:12]3)[CH:16]=2)=[O:25])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 773174-PyridinemethanamineHCID 15547189HCID 15547189, compound

Product 1

HCID 15547190HCID 15547190, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

Sodium hydride (60%, 1.14 g) is suspended in 21 mL of THF. While stirring at about 10° C., a solution of 0.93 g of 4-aminomethylpyridine (8.6 mmoles) in 21 mL of THF is added dropwise. After about 15 minutes, the previously prepared solution of 1-cyclopropylmethyl-7-azaindole-3-carboxylic acid chloride is added dropwise to the reaction mixture. Subsequently, the whole is refluxed for 3 hours. After cooling, the reaction mixture is mixed with 36 mL of ethyl acetate and 36 mL of water. The phases are separated and the organic phase is washed with water. The solvent is distilled off and the residue recrystallized from ethanol.

Workup

  1. temperatureSubsequently, the whole is refluxed for 3 hours
  2. temperatureAfter cooling
  3. customThe phases are separated
  4. washthe organic phase is washed with water
  5. distillationThe solvent is distilled off
  6. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-c1d7fa6a13784cd6809746af4bad8be4
Source dataset
uspto-grants-2007_01
Patent number
US07169787B2

Reaction notes

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