Pyridine → HCID 69603267, compound

HRID 1828474Notes

Reaction equation

HRID 1828474 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([CH2:13][C:14](Cl)=[O:15])=[N:9]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH:25]([C:28]1[N:29]=[C:30]([CH2:33][CH2:34][C:35]2[CH:51]=[CH:50][N:38]3[C:39](=[O:49])[CH:40]=[C:41]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[N:42]=[C:37]3[CH:36]=2)[S:31][CH:32]=1)([CH3:27])[CH3:26]>C(Cl)Cl>[CH:25]([C:28]1[N:29]=[C:30]([CH2:33][CH2:34][C:35]2[CH:51]=[CH:50][N:38]3[C:39](=[O:49])[C:40]([C:14](=[O:15])[CH2:13][C:10]4[N:11]=[N:12][N:8]([CH2:7][C:6]5[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[N:9]=4)=[C:41]([N:43]4[CH2:44][CH2:45][O:46][CH2:47][CH2:48]4)[N:42]=[C:37]3[CH:36]=2)[S:31][CH:32]=1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049Pyridine3×HCID 22063579HCID 22063579, compoundHCID 22063674HCID 22063674, compound3×

Product 1

HCID 69603267HCID 69603267, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]ethanoyl chloride (0.27 g, 1.05 mmol) obtained in (C) was dissolved in methylene chloride (3 ml), added dropwise with pyridine (170.2 μl, 2.10 mmol) under ice cooling, and added dropwise with a solution of 8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4 H-pyrido-[1,2-a]pyrimidin-4-one (80.9 mg, 0.21 mmol) in methylene chloride (3 ml). The reaction solution was stirred at room temperature for 23 hours, then further added with a solution of 2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]ethanoyl chloride (0.27 g, 1.05 mmol) in methylene chloride (2 ml) and pyridine (170.2 μl, 2.10 mmol) under ice cooling. Further, the reaction solution was added with the same amounts of the acid chloride and pyridine twice every 24 hours, and stirred at room temperature. The solvent was evaporated, and the residue was added with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by preparative TLC (hexane:ethyl acetate=1:1, v/v and chloroform:methanol=30:1, v/v) to obtain the title compound (10.1 mg, 7.8%) as yellow oil.

Workup

  1. stirringstirred at room temperature
  2. customThe solvent was evaporated
  3. additionthe residue was added with saturated aqueous sodium hydrogencarbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by preparative TLC (hexane

Sources & evidence

ORD record
ord-926c2159091642cba26443f5cdb1f7cd
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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