Diisopropylethylamine → HCID 59278286, compound

HRID 2198225Notes

Reaction equation

HRID 2198225 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=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.Cl.[CH3:54][S:55]([C:58]1[CH:63]=[C:62]([C@@H:64]([NH2:67])[CH2:65][CH3:66])[CH:61]=[CH:60][N:59]=1)(=[O:57])=[O:56].C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[CH3:54][S:55]([C:58]1[CH:63]=[C:62]([C@@H:64]([NH:67][C:17]([C:16]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:12]=3[CH:13]=[N:14][CH:15]=2)=[O:19])[CH2:65][CH3:66])[CH:61]=[CH:60][N:59]=1)(=[O:57])=[O:56]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acidHCID 66727359HCID 66727359, compound

Product 1

HCID 59278286HCID 59278286, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (1.08 g, 4.20 mmol) and DIPEA (2.19 ml, 12.6 mmol) in DMF (20 mL) was added HATU (3.19 g, 8.39 mmol). After 30 minutes, a solution of (S)-1-(2-methanesulfonyl-pyridin-4-yl)-propylamine hydrochloride salt (0.90 g, 4.2 mmol) in DCM (1 mL) was added, and the reaction mixture became homogeneous. After 16 hours, the mixture was poured into saturated aqueous NaHCO3, and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The crude material was twice purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford a yellow solid. The solid was dissolved in a minimal amount of dichloromethane and diluted with hexanes, and the collected by filtration washing with diethyl ether to afford the title compound as an off-white solid.

Workup

  1. waitAfter 16 hours
  2. extractionextracted with dichloromethane (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was twice purified by silica gel chromatography
  8. washeluting with a gradient of 0-100% EtOAc in hexanes
  9. customto afford a yellow solid
  10. filtrationthe collected by filtration
  11. washwashing with diethyl ether

Sources & evidence

ORD record
ord-73fbe58c7ee94cbfbd0b4dfccf017190
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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