Ethyl Acetate → HCID 66842146, compound

HRID 251837Notes

Reaction equation

HRID 251837 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[N:11]1.Cl[C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)=[O:21].C(OCC)(=O)C>CN(C)C1C=CN=CC=1.O1CCCC1.O>[N:10]1([C:20]([N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[O:21])[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[N:11]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 178420751HCID 178420751, compound

Product 1

HCID 66842146HCID 66842146, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.39 ml (8.40 mmol) of diisopropylethylamine are added to a suspension of 0.840 g (7 mmol) of 1H-[1,2,3]triazolo[4,5-b]pyridine, of 1.741 g (7 mmol) of tert-butyl 4-chlorocarbonylpiperazine-1-carboxylate (Bioorg. Med. Chem. Lett. 2000, 10, 2357) and of 0.042 g (0.35 mmol) of 4-dimethylaminopyridine in 14 ml of tetrahydrofuran. The mixture is stirred at ambient temperature for 4 hours and then 80 ml of ethyl acetate and 20 ml of water are added. The organic phase is separated by settling out and is then washed with 3×20 ml of water and 20 ml of a saturated aqueous solution of sodium chloride. The product is dried over sodium sulfate and evaporated to dryness. The residue is recrystallized from isopropanol, so as to obtain 1.70 g (5.1 mmol) of product in the form of white crystals.

Workup

  1. customThe organic phase is separated
  2. washis then washed with 3×20 ml of water and 20 ml of a saturated aqueous solution of sodium chloride
  3. dry with materialThe product is dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-56f3b6d9115647808e5d5e0f0e78ffdb
Source dataset
uspto-grants-2011_01
Patent number
US07868007B2

Reaction notes

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