Ethylamine → HCID 71293415, compound

HRID 2362312Notes

Reaction equation

HRID 2362312 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[C:15](=[O:18])[NH:16][N:17]=[C:13]3[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:11]([CH3:29])=[C:10]2[C:30](O)=[O:31])=[CH:5][CH:4]=1)#[N:2].[CH3:33][CH2:34][N:35](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)C>CN(C=O)C>[CH2:34]([NH:35][C:30]([C:10]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:14]2[C:15](=[O:18])[NH:16][N:17]=[C:13]2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:11]=1[CH3:29])=[O:31])[CH3:33]

Participants

6

Reactant 4

HCID 6341Ethylamine2×HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71293434HCID 71293434, compound

Product 1

HCID 71293415HCID 71293415, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 9 (100 mg, 0.23 mmol) in DMF (3 ml), were added DIPEA (102 μl, 0.6 mmol) and HATU (133 mg, 0.35 mmol) and the reaction mixture was stirred at RT for 45 mins. Ethylamine (2 M in THF, 175 μL, 0.35 mmol) was then added, and stirring at RT was continued for 16 hours. Further ethylamine (2 M in THF, 175 μL, 0.35 mmol) was added, the temperature was raised to 60° C., and stirring was continued for 1.5 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 80-100% EtOAc in cyclohexane to yield the title compound as a white solid (53 mg).

Workup

  1. stirringstirring at RT
  2. waitwas continued for 16 hours
  3. temperaturethe temperature was raised to 60° C.
  4. stirringstirring
  5. waitwas continued for 1.5 hours
  6. customThe reaction mixture was partitioned between EtOAc and water
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo
  11. customThe resulting residue was purified by silica gel chromatography
  12. washeluting with a gradient of 80-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-6310e869927d4f9bbd75311b192909e4
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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