Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86693907, compound

HRID 1466742Notes

Reaction equation

HRID 1466742 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].[C@H:23]12[CH2:29][C@H:26]([NH:27][CH2:28]1)[CH2:25][N:24]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([N:27]1[CH2:28][C@@H:23]2[CH2:29][C@H:26]1[CH2:25][N:24]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:5]

Participants

5

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 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 248117402-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

Product 1

HCID 86693907HCID 86693907, compoundYield 194.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (400 mg, 1.32 mmol), (1S,4S)-tert-butyl 2,5-diazabicyclo[2,2,1]heptane-2-carboxylate (665 mg, 3.35 mmol), HATU (1.02 g, 2.68 mmol), and DI PEA (1.2 ml, 6.7 mmol) were dissolved in DMF (25 ml) and stirred at room temperature for 72 h. The reaction mixture was partitioned between DCM and water (50 ml each), and the organic phase was washed with aqueous sodium bicarbonate and brine, dried over sodium sulphate, filtered, and concentrated to get the crude product (1.23 g) as brown oil, used in next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between DCM and water (50 ml each)
  2. washthe organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b9abd55b0d64042afb250070643765a
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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