Diisopropylethylamine → HCID 131735533, compound

HRID 522406Notes

Reaction equation

HRID 522406 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:34]([O:41][C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[N:45]=[C:44]([O:52][C@@H:53]2[CH2:57][C@@H:56]([C:58]([O:60][CH3:61])=[O:59])[NH:55][CH2:54]2)[C:43]=1[C:62]#[C:63][CH2:64][CH2:65][CH2:66][C@@H:67]1[CH2:69][C@H:68]1[O:70][C:71]([NH:73][C@@H:74]([C:78]1([CH3:84])[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]1)[C:75](O)=[O:76])=[O:72])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[CH2:34]([O:41][C:42]1[C:51]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[N:45]=[C:44]2[O:52][C@H:53]3[CH2:54][N:55]([C:75](=[O:76])[C@H:74]([C:78]4([CH3:84])[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83]4)[NH:73][C:71](=[O:72])[O:70][C@@H:68]4[CH2:69][C@H:67]4[CH2:66][CH2:65][CH2:64][C:63]#[C:62][C:43]=12)[C@H:56]([C:58]([O:60][CH3:61])=[O:59])[CH2:57]3)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117598819HCID 117598819, compound

Product 1

HCID 131735533HCID 131735533, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A round-bottom flask was charged with HATU (1711 mg, 4.50 mmol) and dry DMF (2.25E+04 μl) at 0° C. N,N-diisopropylethylamine (1531 μl, 9.00 mmol) was added followed by addition of a solution of the product of step 3 (1827 mg, 2.25 mmol) in dry DMF (2.25E+04 μl) via syringe pump over 1 hour. After addition was complete the reaction was stirred at room temperature for 2 hours. LCMS and MS analyses showed a complete reaction. The reaction mixture was concentrated to almost dryness in rotavap (high vacuum) and the residue was diluted with ethyl acetate (200 mL). The mixture was washed with water (50 mL), aq. 1M HCl (50 mL), half-saturated sodium bicarbonate (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in rotavap. The residue was purified on a Redisep (120 g) silica gel column (gradient: 0 to 40% ethyl acetate in hexanes) to give the title compound (900 mg, 1.324 mmol, 58.8% yield) as a white powder.

Workup

  1. additionAfter addition
  2. customa complete reaction
  3. concentrationThe reaction mixture was concentrated to almost dryness in rotavap (high vacuum)
  4. additionthe residue was diluted with ethyl acetate (200 mL)
  5. washThe mixture was washed with water (50 mL), aq. 1M HCl (50 mL), half-saturated sodium bicarbonate (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in rotavap
  9. customThe residue was purified on a Redisep (120 g) silica gel column (gradient: 0 to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1862cde136ed4dfd8bc98be504155712
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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