3-(Dimethylamino)-1-propanol → HCID 71293473, compound

HRID 570884Notes

Reaction equation

HRID 570884 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]([CH2:60][CH2:61][CH2:62]O)[CH3:59]>CN(C=O)C>[CH3:57][N:58]([CH3:59])[CH2:60][CH2:61][CH2:62][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 766463-(Dimethylamino)-1-propanolHCID 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 71293473HCID 71293473, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 9 (42 mg, 0.095 mmol) in DMF (1 mL), was added diiosopropylethylamine (33 μL, 0.19 mmol) followed by HATU (72 mg, 0.19 mmol). After 1 hour, N, N-dimethylpropanolamine (67 μL, 0.57 mmol) was added, and the reaction mixture was stirred at 60° C. for 16 hours. The reaction mixture was allowed to cool to RT then 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 0-6% (2 M NH3 in MeOH) in DCM to give the title compound as a white solid (15 mg).

Workup

  1. temperatureto cool to RT
  2. customthen partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer further extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-6% (2 M NH3 in MeOH) in DCM

Sources & evidence

ORD record
ord-49e7b392977b46cca2d27cd6373aee1c
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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