Diisopropylethylamine → HCID 44227504, compound

HRID 2068637Notes

Reaction equation

HRID 2068637 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=2)[CH:3]=[N:2]1.Cl.[CH3:15][C:16]1([CH3:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:15][C:16]1([CH3:22])[CH2:21][CH2:20][N:19]([C:11]([C:8]2[CH:7]=[C:6]([C:4]3[CH:5]=[N:1][NH:2][CH:3]=3)[S:10][CH:9]=2)=[O:13])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222529024,4-Dimethylpiperidinium chlorideHCID 581101935-(1H-Pyrazol-4-YL)thiophene-3-carboxylic acid

Product 1

HCID 44227504HCID 44227504, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.075 g, 0.39 mmol) and 4,4-dimethylpiperidine hydrochloride (0.087 g, 0.58 mmol) were dissolved in DMF (3 mL) then DIPEA (0.2 g, 1.55 mmol) and HATU (0.175 g, 1.55 mmol) were added and the reaction mixture was stirred at room temperature overnight. The solvent was removed by evaporation then the residue was dissolved in DCM and washed with aqueous sodium hydrogen carbonate solution. The organics were dried by evaporation. The crude material was purified by HPLC, eluting with 5%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were freeze-dried to give the title compound (0.063 g). LCMS m/z 290.18 [M+H]+ R.T.=8.74 min (Analytical Method 2).

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with aqueous sodium hydrogen carbonate solution
  4. customThe organics were dried by evaporation
  5. customThe crude material was purified by HPLC
  6. washeluting with 5%-98% acetonitrile in water (0.1% formic acid) over 20 minutes
  7. additionThe fractions containing the desired product
  8. customwere freeze-dried

Sources & evidence

ORD record
ord-1383266dc26e44d6917e6b98e37402c9
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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