2-(Dimethylamino)ethanol → HCID 71293454, compound

HRID 570883Notes

Reaction equation

HRID 570883 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]([OH:32])=[O:31])=[CH:5][CH:4]=1)#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:57][N:58]([CH3:62])[CH2:59][CH2:60]O>CN(C=O)C>[CH3:57][N:58]([CH3:62])[CH2:59][CH2:60][O:31][C:30]([C:10]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=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:27])([F:28])[F:26])[CH:20]=2)[C:11]=1[CH3:29])=[O:32]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 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 71293454HCID 71293454, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 9 (32 mg, 0.073 mmol) in DMF (1 mL), was added diiosopropylethylamine (125 μL, 0.73 mmol) followed by HATU (30 mg, 0.080 mmol). After 1 hour, N,N-dimethylethanolamine (73 μL, 0.73 mmol) was added, and the reaction mixture was stirred at RT for 16 hours. 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 reverse phase HPLC using a gradient 20-70% acetonitrile in water with 0.1% ammonia to yield the title compound as a white solid (4 mg).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-200e08c9e2ab4e9da6e08b7043781631
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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