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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 662127
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 662127
[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[N:28]=[C:27]([C:29]([OH:31])=O)[CH:26]=[CH:25][CH:24]=3)=[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].[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([CH2:41][C:42]2[CH:43]=[C:44]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][NH2:55])[CH:49]=3)[CH:45]=[CH:46][CH:47]=2)[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CS(C)=O.C(Cl)Cl>[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]=[CH:25][CH:26]=[C:27]([C:29]([NH:55][CH2:54][C:50]4[CH:49]=[C:48]([C:44]5[CH:45]=[CH:46][CH:47]=[C:42]([CH2:41][CH:38]6[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]6)[CH:43]=5)[CH:53]=[CH:52][CH:51]=4)=[O:31])[N:28]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813254({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amineHCID 578193746-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid

Produkt 1

HCID 44193617
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
Ausbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Process (B) In an alternate preparation of the titled compound, to a solution 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 (45 mg, 0.1 mmol) in DMSO (1 mL) was added 1-{3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methanamine (28 mg, 0.095 mmol), HBTU (42 mg, 0.11 mmol) and Et3N (0.021 mL, 0.15 mmol) in DCM (3 mL). The resulting mixture was stirred at room temperature for 18 h. The reaction was quenched with H2O (2 drops), purified with a Gilson HPLC (with 0.1% TFA), concentrated, re-dissolved in EtOAc, washed with NaOH (1N), dried over Na2SO4, filtered, concentrated and dried with a high vacuum oil pump to afford the title compound as a white solid 38.5 mg (53%). LC-MS m/z 729 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with H2O (2 drops)
  2. custompurified with a Gilson HPLC (with 0.1% TFA)
  3. concentrationconcentrated
  4. dissolutionre-dissolved in EtOAc
  5. washwashed with NaOH (1N)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried with a high vacuum oil

Quellen und Nachweise

ORD-Eintrag
ord-8bbb316d57604737bee1017f8eef5e1f
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084449B2

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