1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 71293445, compound

HRID 570889Notes

Reaction equation

HRID 570889 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:26])[N:20]([CH2:22][C:23](O)=[O:24])[N:21]=[C:8]2[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[C:6]=1[CH3:37])=[O:4].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:71][NH:72][CH2:73][CH2:74][N:75]([CH3:77])[CH3:76]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:26])[N:20]([CH2:22][C:23](=[O:24])[N:72]([CH2:73][CH2:74][N:75]([CH3:77])[CH3:76])[CH3:71])[N:21]=[C:8]2[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:34])[F:36])[CH:28]=2)[C:6]=1[CH3:37])=[O:4]

Participants

6

Reactant 4

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 71293468HCID 71293468, compound

Product 1

HCID 71293445HCID 71293445, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 17 (48 mg, 0.09 mmol) was dissolved in DMF (1 mL), and then diisopropylethylamine (48 μL, 0.28 mmol) and HATU (39 mg, 0.10 mmol) were added. The reaction mixture was stirred at RT for 30 minutes and then N,N,N-trimethylethylenediamine (36 μL, 0.28 mmol) was added. After 3 hours of stirring at RT, another portion of HATU was added (10 mg, 0.03 mmol), and stirring was continued for 1 hour. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-10% (2M NH3 in MeOH) in DCM to give the title compound as a white solid (40 mg).

Workup

  1. stirringAfter 3 hours of stirring at RT
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customThe reaction mixture was partitioned between EtOAc and water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer further extracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe resulting residue was purified by silica gel chromatography
  11. washeluting with a gradient of 0-10% (2M NH3 in MeOH) in DCM

Sources & evidence

ORD record
ord-a733eb7b50a54e4b94546797b2912aec
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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