Diisopropylethylamine → HCID 68552023, compound

HRID 2189947Notes

Reaction equation

HRID 2189947 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C@@H:27]([CH3:31])[C:28]([OH:30])=O.CCN(C(C)C)C(C)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=1[C:49]1[S:53][C:52]([CH2:60][O:61][CH2:62][C:63]#[N:64])([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[NH:51][N:50]=1>CN(C=O)C.C([O-])(O)=O.[Na+]>[F:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=1[C:49]1[S:53][C:52]([CH2:60][O:61][CH2:62][C:63]#[N:64])([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:51]([C:28](=[O:30])[C@@H:27]([O:26][CH3:25])[CH3:31])[N:50]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 57025662-methoxypropanoic acid, (S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68549417HCID 68549417, compound

Product 1

HCID 68552023HCID 68552023, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of HATU (0.0776 g, 0.2041 mmol) in 0.5 mL of DMF was added (S)-2-methoxy propanoic acid (0.0150 ml, 0.2041 mmol) and DIEA (0.0711 ml, 0.4083 mmol). This mixture was stirred at room temperature for 10 minutes and the crude mixture from Step D (0.047 g) was then added followed by 0.2 mL of DMF. The reaction mixture was stirred at room temperature for 40 hours. The reaction mixture was as diluted with saturated NaHCO3 and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel chromatography (20% EtOAc in hexanes) provided 3.5 mg of a cloudy film that contained the desired product as the primary component. This mixture was used in the subsequent step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 40 hours
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel chromatography (20% EtOAc in hexanes)
  8. customprovided 3.5 mg of a cloudy film that

Sources & evidence

ORD record
ord-fe84add8e3a346caa8ed5e507bba95ed
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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