Pyridine → HCID 58136386, compound

HRID 877178Notes

Reaction equation

HRID 877178 reaction equation
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH2:33][C:34]([CH3:44])([C:40]([O:42][CH3:43])=[O:41])[CH2:35]2.N1C=CC=CC=1>CN(C=O)C>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7]([NH:30][C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH2:33][C:34]([CH3:44])([C:40]([O:42][CH3:43])=[O:41])[CH2:35]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 58074507cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acidHCID 58136508HCID 58136508, compound

Product 1

HCID 58136386HCID 58136386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 mg (0.97 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid (enantiomer 2, Example 77A), 459 mg (1.2 mmol) of methyl 4-amino-2-methyl-2,3-dihydro-1H-indene-2-carboxylate (Example 95A), 556 mg (1.46 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) and 5 ml of pyridine in 20 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the reaction mixture was poured onto ice-water, the phases were separated and the aqueous phase was extracted three times with tert-butyl methyl ether. The combined organic phases were dried over sodium sulfate, and after filtration the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by preparative HPLC. This gave 448 mg (0.77 mmol, 79% of theory) of a colorless oil.

Workup

  1. additionthe reaction mixture was poured onto ice-water
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with tert-butyl methyl ether
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationafter filtration the solvent
  6. customwas removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-602269bf2fb24c569fc478ceda38387d
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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