Triethylamine → N-{[3-bromo-5-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

HRID 564534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564534
[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]([OH:28])=O)=[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].[Br:34][C:35]1[CH:36]=[C:37]([CH2:43]N)[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1.C[N:46](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[Br:34][C:35]1[CH:36]=[C:37]([CH2:43][N:20]([CH2:19][C:10]2[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]3[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]3=[N:8][C:9]=2[CH2:32][CH3:33])[C:21]([C:23]2[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([NH2:46])=[O:28])[CH:24]=2)=[O:22])[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534144413-Bromo-5-methoxybenzenemethanamineHCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

Produkt 1

HCID 67006812N-{[3-bromo-5-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (762 mg, 1.69 mmol), {[3-bromo-5-(methyloxy)phenyl]methyl}amine (529 mg, 1.86 mmol), HBTU (769 mg, 2.03 mmol) and Et3N (0.47 mL, 3.38 mmol) in DCM was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 and extracted with DCM twice. The combined organic layers were then washed with water followed by a brine wash. The organic layer was then concentrated under vacuum to give a crude residue. It was then purified using CombiFlash chromatography eluting with 0 to 10% methanol in DCM to obtain N-{[3-bromo-5-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide as a solid (1.05 g, 96%). LC-MS m/z 649 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were then washed with water
  4. washwash
  5. concentrationThe organic layer was then concentrated under vacuum
  6. customto give a crude residue
  7. customIt was then purified
  8. washeluting with 0 to 10% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-f192a86c6bd4431296b7857d74f7749c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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