Diisopropylethylamine → HCID 68322457, compound

HRID 1505361Notes

Reaction equation

HRID 1505361 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])[CH3:3].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.[CH3:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[C:50]=1[O:56][C:57]1[N:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=1>CN(C)C=O>[CH3:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[C:50]=1[O:56][C:57]1[N:62]=[CH:61][C:60]([NH:63][C:11](=[O:13])[C:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:10])[CH3:14])=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16641867HCID 16641867, compound2×

Product 1

HCID 68322457HCID 68322457, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 8 mL vial N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methylalanine (204 mg, 1.003 mmol) and N-ethyl-N-(1-methylethyl)-2-propanamine (0.219 mL, 1.253 mmol) were dissolved in N,N-Dimethylformamide (4 mL) to give a pale yellow solution. N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (381 mg, 1.003 mmol) was added. The reaction mixture became bright yellow and was stirred at room temperature for 15 minutes. 6-[(2,6-dimethylphenyl)oxy]-3-pyridinamine (Intermediate 42, 223.8 mg) was added and the reaction mixture was warmed at 60° C. After 4 hours, the reaction was complete. The solvent was evaporated under vacuum using the Genevac affording a dark brown oil which was purified by silica gel chromatography (Biotage system, 25 g SNAP column) using as eluents a gradient Cyclohexane/EtOAc from 3:1 to 1:1 in 10 CV; then 1:1 for 5 CV. The collected fractions afforded the title compound as a pale yellow solid (202.1 mg).

Workup

  1. customto give a pale yellow solution
  2. temperaturethe reaction mixture was warmed at 60° C
  3. waitAfter 4 hours
  4. customThe solvent was evaporated under vacuum
  5. customaffording a dark brown oil which
  6. customwas purified by silica gel chromatography (Biotage system, 25 g SNAP column)

Sources & evidence

ORD record
ord-20d829da08cd453e982d3e7ecde249d9
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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