Ethyl Acetate → HCID 15547190, compound

HRID 2245278Notes

Reaction equation

HRID 2245278 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-5256d2bf350242d78b444483db79bf32
Source dataset
uspto-grants-2010_03
Patent number
US07683074B2

Reaction notes

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