Water → HCID 70191874, compound

HRID 1384922Notes

Reaction equation

HRID 1384922 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:18][CH2:17][CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9]1.Cl[C:20]1[N:21]=[CH:22][C:23]2[CH:29]=[CH:28][CH2:27][N:26]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]4[O:38][CH2:39][O:40][C:34]=4[CH:33]=3)[C:24]=2[N:25]=1.O>O1CCCC1>[CH2:15]([O:14][C:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:20]2[N:21]=[CH:22][C:23]3[CH:29]=[CH:28][CH2:27][N:26]([NH:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]5[O:38][CH2:39][O:40][C:34]=5[CH:33]=4)[C:24]=3[N:25]=2)[CH2:18][CH2:17]1)=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 86583777HCID 86583777, compound

Product 1

HCID 70191874HCID 70191874, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

41 mg of triethylamine and 190 mg of ethyl isonipecotate were added to a solution of 127 mg of 2-chloro-8-(3,4-methylenedioxybenzyl)aminopyrido[2,3-d]pyrimidine in 8 ml of tetrahydrofuran. The obtained mixture was refluxed for 2 hours, followed by the addition of water. The resulting mixture was extracted with chloroform twice. The organic layers were combined, dried over magnesium sulfate, and distilled to remove the solvent. The residue was purified by silica gel chromatography (with ethyl acetate) to give 175 mg of the title compound (in a yield of 100%).

Workup

  1. temperatureThe obtained mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with chloroform twice
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel chromatography (with ethyl acetate)

Sources & evidence

ORD record
ord-873203a1915641eabaf531cb56caa0c1
Source dataset
uspto-grants-2001_07
Patent number
US06262059B1

Reaction notes

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