Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 58288419, compound

HRID 1476115Notes

Reaction equation

HRID 1476115 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([C@@H:29]([CH3:34])[C:30]([F:33])([F:32])[F:31])[C:26](O)=[O:27])=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1.CN(C=O)C.C(OCC)(=O)C>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([CH:9]([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:3][C:2]=1[NH:1][C:26](=[O:27])[C@H:25]([C:22]1[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][CH:23]=1)[C@@H:29]([CH3:34])[C:30]([F:31])([F:32])[F:33]

Participants

7

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58288396(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acidHCID 58288401HCID 58288401, compound

Product 1

HCID 58288419HCID 58288419, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.45 g (5.67 mmol) of (+/−)-methyl 3-(3-amino-4-chlorophenyl)hexanoate and 1.81 g (6.80 mmol) of (+)-(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid were dissolved in 5.0 ml of pyridine and 10.0 ml of DMF, and 2.80 g (7.37 mmol) of HATU were added at RT. The reaction mixture was stirred at RT overnight and then diluted with ethyl acetate. The mixture was washed with 1 N hydrochloric acid and sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase initially cyclohexane, then cyclohexane/ethyl acetate 50:1). In two fractions, in total 2.02 g of the target product were obtained (70.6% of theory).

Workup

  1. washThe mixture was washed with 1 N hydrochloric acid and sat. sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel (mobile phase initially cyclohexane

Sources & evidence

ORD record
ord-e106b4960585447794047f1fcb3bf88d
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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