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Triethylamine → N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide

HRID 662126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 662126
CC(C1CN(CC2C=C(C3C=C(CNC(C4C=CC=C(C(NC[C:38]5[C:39]([NH:51][CH:52]6[CH2:57][CH2:56][O:55][CH2:54][CH2:53]6)=[C:40]6[CH:48]=[N:47][N:46]([CH2:49][CH3:50])[C:41]6=[N:42][C:43]=5[CH2:44][CH3:45])=O)N=4)=O)C=CC=3C)C=CC=2)CCN1C([O-])=O)(C)C.C(N1[C:68]2=N[C:70]([CH2:93][CH3:94])=[C:71]([CH2:80][NH:81][C:82]([C:84]3[N:89]=[C:88]([C:90]([OH:92])=O)[CH:87]=[CH:86][CH:85]=3)=[O:83])[C:72](NC3CCOCC3)=[C:67]2C=N1)C.NCC1C=[C:99]([C:103]2C=C[CH:106]=[C:105]([CH2:109][CH:110]3[CH2:115][CH2:114][N:113]([C:116](OC(C)(C)C)=O)[CH2:112][CH2:111]3)[CH:104]=2)C=CC=1.[CH3:123][N:124](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[CH2:49]([N:46]1[C:41]2=[N:42][C:43]([CH2:44][CH3:45])=[C:38]([CH2:123][NH:124][C:90]([C:88]3[CH:87]=[CH:86][CH:85]=[C:84]([C:82]([NH:81][CH2:80][C:71]4[CH:70]=[C:93]([C:94]5[CH:99]=[CH:103][CH:104]=[C:105]([CH2:109][CH:110]6[CH2:115][CH2:114][N:113]([CH3:116])[CH2:112][CH2:111]6)[CH:106]=5)[CH:68]=[CH:67][CH:72]=4)=[O:83])[N:89]=3)=[O:92])[C:39]([NH:51][CH:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[C:40]2[CH:48]=[N:47]1)[CH3:50]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813360tert-Butyl 4-{[3'-(aminomethyl)biphenyl-3-yl]methyl}piperidine-1-carboxylateHCID 578193746-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid
HCID 86633354
1,1-Dimethylethyl-4-[(5'-{[({6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinyl}carbonyl)amino]methyl}-2'-methyl-3-biphenylyl)methyl]-1-piperazinecarboxylate

Produkt 1

HCID 44193617N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamideAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Process (A) A mixture of 6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid (84 mg, 0.186 mmol), 1,1-dimethylethyl 4-{[3′-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate (54.7 mg, 0.186 mmol), HBTU (o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (84 mg, 0.223 mmol) and Et3N (0.129 mL, 0.928 mmol) in DCM (3 mL) was stirred at room temperature overnight. The crude mixture was quenched with saturated NaHCO3, and extracted with DCM twice. The combined organic layers were washed with brine and then concentrated under vacuum to give crude residue. The crude product was purified with a Gilson HPLC (with 0.1% TFA in the solvents), eluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min. The product fractions were combined, converted to the free base with saturated NaHCO3 and the basified solution was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-({3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide as a white solid (30 mg, 22.2%). LC-MS m/z 729 (M+H)+, 0.80 min (ret time).

Aufarbeitung

  1. customThe crude mixture was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated under vacuum
  5. customto give crude residue
  6. customThe crude product was purified with a Gilson HPLC (with 0.1% TFA in the solvents),
  7. washeluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min
  8. extractionthe basified solution was extracted with ethyl acetate twice
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a4dc6b71f51849aca2669394241d3e6f
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084449B2

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