Diisopropylethylamine → HCID 46947748, compound

HRID 1946364Notes

Reaction equation

HRID 1946364 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:11])[C:7]=1[C:8]([OH:10])=O.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.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][N:54]1[CH:58]=[CH:57][C:56]([NH2:59])=[N:55]1>CN(C)C=O>[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][N:54]1[CH:58]=[CH:57][C:56]([NH:59][C:8]([C:7]2[C:6]([F:11])=[CH:5][N:4]=[CH:3][C:2]=2[F:1])=[O:10])=[N:55]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 53027431-((2,4-Dichlorophenyl)methyl)-1H-pyrazol-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 201118793,5-Difluoroisonicotinic acid

Product 1

HCID 46947748HCID 46947748, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 3,5-difluoro-4-pyridinecarboxylic acid (15.9 mg, 0.1 mmol, Frontier Scientific) in dimethylformamide (0.1 ml) was added HATU (38 mg, 0.1 mmol) in dimethylformamide (0.2 mL), followed by N,N-diisopropylethylamine (0.050 ml, 0.286 mmol) and the resulting solution left for 5 min. Finally, a solution of 1-[(2,4-dichlorophenyl)methyl]-1H-pyrazol-3-amine (24.2 mg, 0.01 mmol, ChemCollect GmbH) in N,N-dimethylformamide (0.1 ml) was added and the resulting solution shaken for 10 min. The solution was then left to stand for 16 h at ambient temperature after which the solvent was removed. A 1:1 mixture of dimethylsulphoxide:methanol (0.6 ml) was added and the solution purified by MDAP on SUNFIRE C18 column (Method D). The appropriate fraction was concentrated in vacuo then under nitrogen flow to give the title compound (4.4 mg);

Workup

  1. waitThe solution was then left
  2. waitto stand for 16 h at ambient temperature
  3. customafter which the solvent was removed
  4. additionA 1:1 mixture of dimethylsulphoxide
  5. additionmethanol (0.6 ml) was added
  6. customthe solution purified by MDAP on SUNFIRE C18 column (Method D)
  7. concentrationThe appropriate fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-d6fc68505d82465ca40555083e90a95b
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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