Pyridine → Methyl (2E)-3-{2-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)-methyl]phenyl}butanoyl)amino]phenyl}prop-2-enoate

HRID 877185Notes

Reaction equation

HRID 877185 reaction equation
[CH3:1][CH:2]([CH3:27])[CH:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:19](=[O:20])[CH2:18][O:17][C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:15]2)=[CH:9][CH:8]=1)[C:4](O)=[O:5].[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1/[CH:35]=[CH:36]/[C:37]([O:39][CH3:40])=[O:38].N1C=CC=CC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][CH:2]([CH3:27])[CH:3]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][N:14]2[C:19](=[O:20])[CH2:18][O:17][C:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:15]2)=[CH:11][CH:12]=1)[C:4]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1/[CH:35]=[CH:36]/[C:37]([O:39][CH3:40])=[O:38])=[O:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11240788HCID 11240788, compoundHCID 581363843-methyl 2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoic acid

Product 1

HCID 58136695Methyl (2E)-3-{2-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)-methyl]phenyl}butanoyl)amino]phenyl}prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50 mg (0.14 mmol) of 3-methyl 2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoic acid (enantiomer 2; Example 79A), 20 mg (0.11 mmol) of methyl (2E)-3-(2-aminophenyl)prop-2-enoate, 1.5 ml of pyridine and 65 mg (0.17 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) in 5 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 7 mg (0.01 mmol, 9.8% 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-4090b553f7134933a5cf0509168a5a2d
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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