Diisopropylethylamine → HCID 59547904, compound

HRID 1946425Notes

Reaction equation

HRID 1946425 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][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.CCN(C(C)C)C(C)C.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][N:53]2[CH:57]=[CH:56][C:55]([NH2:58])=[N:54]2)=[C:48]([C:59]([F:62])([F:61])[F:60])[CH:47]=1>CN(C)C=O.CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:58][C:55]1[CH:56]=[CH:57][N:53]([CH2:52][C:49]2[CH:50]=[CH:51][C:46]([O:45][CH3:44])=[CH:47][C:48]=2[C:59]([F:61])([F:60])[F:62])[N:54]=1)=[O:10]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27358163-Chloropyridine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59547879HCID 59547879, compound

Product 1

HCID 59547904HCID 59547904, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-4-pyridinecarboxylic acid (103 mg, 0.654 mmol, Aldrich) in N,N-dimethylformamide (0.5 ml) was added HATU (250 mg, 0.657 mmol), DIPEA (0.27 ml, 1.55 mmol) and then 1-{[4-(methyloxy)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (for a preparation see Intermediate 52)(135 mg, 0.498 mmol). The resulting brown solution was stirred at ambient temperature for 30 min. The reaction mixture was diluted with methanol (1 ml) and purified by MDAP on an Xbridge column using Acetonitrile-Water with an ammonium carbonate modifier (Method E). The solvent was evaporated in vacuo to give the title compound as an orange foam (160 mg); LCMS (System 4) MH+=411, tRET=2.69 min.

Workup

  1. custompurified by MDAP on an Xbridge column
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-20922009d01a480791b4bf70384e6b2b
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

Loading…