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Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-[(3-Bromo-5-chlorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

HRID 564506
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 564506
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26](O)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:58][C:59]1[CH:60]=[C:61]([CH:64]=[C:65]([Cl:67])[CH:66]=1)[CH2:62][NH2:63]>ClCCl>[Br:58][C:59]1[CH:60]=[C:61]([CH2:62][NH:63][C:26]([C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:21]([NH:20][CH2:19][C:10]3[C:11]([NH:12][CH:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)=[C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]4=[N:8][C:9]=3[CH2:32][CH3:33])=[O:22])[CH:24]=2)=[O:27])[CH:64]=[C:65]([Cl:67])[CH:66]=1
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Komponenten

5

Edukt 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidHCID 58962965(3-Bromo-5-chlorophenyl)methanamine

Produkt 1

HCID 57813347N-[(3-Bromo-5-chlorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (677 mg, 1.5 mmol) was suspended in dichloromethane (DCM) (50 ml), and HBTU (569 mg, 1.5 mmol) was added, followed sequentially by 3-bromo-5-chlorobenzylamine (331 mg, 1.5 mmol), and TEA (0.418 mL, 3.0 mmol). The reaction mixture was stirred overnight under argon at room temperature to give a clear-colorless solution. The solvent was removed on a rotovap and the residue was partitioned between ethyl acetate (100 mL) and 1N NaOH (20 mL). The phases were separated and the organic phase was washed 2× with 1N NaOH (20 mL), and then 1× with brine (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was taken up in dichloromethane and absorbed on Isolute® Sorbent and purified by CombiFlash on a 40 g silica column eluted with 0-10% DCM/MeOH to give the title compound as white solid. LC-MS m/z 652.9 (M+H)+, 2.08 min (ret time); mp 109-112° C.; analytical HPLC shows 97.6% purity, (ret time 13.921 min).

Aufarbeitung

  1. customto give a clear-colorless solution
  2. customThe solvent was removed on a rotovap
  3. customthe residue was partitioned between ethyl acetate (100 mL) and 1N NaOH (20 mL)
  4. customThe phases were separated
  5. washthe organic phase was washed 2× with 1N NaOH (20 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product
  10. customabsorbed on Isolute® Sorbent
  11. custompurified by CombiFlash on a 40 g silica column
  12. washeluted with 0-10% DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-6d3595c33b4049029f4330732ddbca92
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08067408B2

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