Diisopropylethylamine → HCID 59278286, compound

HRID 1361254Notes

Reaction equation

HRID 1361254 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-b7eb0c1d8f234f61953e5cf06f11369d
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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