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

HRID 564535
Notes
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Reaction equation

HRID 564535 reaction equation
BrC1C=C(C[NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH:22][CH2:23][C:24]3[C:25]([NH:37][CH:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[C:26]4[CH:34]=[N:33][N:32]([CH2:35][CH3:36])[C:27]4=[N:28][C:29]=3[CH2:30][CH3:31])=[O:21])[CH:15]=2)=[O:13])C=C(OC)C=1.[CH:44]([C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1)=[O:45].[C:55]([O-:58])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:35]([N:32]1[C:27]2=[N:28][C:29]([CH2:30][CH3:31])=[C:24]([CH2:23][N:22]([CH2:12][C:14]3[CH:15]=[C:16]([C:48]4[CH:49]=[CH:50][CH:51]=[C:46]([CH:44]=[O:45])[CH:47]=4)[CH:17]=[C:18]([O:58][CH3:55])[CH:19]=3)[C:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([C:12]([NH2:11])=[O:13])[CH:15]=3)=[O:21])[C:25]([NH:37][CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[C:26]2[CH:34]=[N:33]1)[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 57813286N-{[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

Product 1

HCID 86633199
N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N-{[3'-formyl-5-(methyloxy)-3-biphenylyl]methyl}-1,3-benzenedicarboxamide
Yield 169.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 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 (782 mg, 1.20 mmol), 3-formylphenyl boronic acid (234 mg, 1.57 mmol), Na2CO3 (383 mg, 3.61 mmol), Pd(PPh3)4 (69.6 mg, 0.06 mmol), and water (3 mL) in dioxane (9 mL) was degassed for 5 min. This mixture was then heated under microwave for 30 min at 150° C. It was quenched with water and then extracted with ethyl acetate twice. The combined organic layers were washed with water and brine. The organic layer was filtered though a 0.45 μM filter and then concentrated to give a crude residue. It was then purified with Combi Flash chromatography eluting with 0 to 10% MeOH in DCM. The product fractions were combined and 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′-formyl-5-(methyloxy)-3-biphenylyl]methyl}-1,3-benzenedicarboxamide as a solid (687 mg, 85%). LC-MS m/z 676 (M+H)+.

Workup

  1. customwas degassed for 5 min
  2. customIt was quenched with water
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic layers were washed with water and brine
  5. filtrationThe organic layer was filtered though a 0.45 μM
  6. filtrationfilter
  7. concentrationconcentrated
  8. customto give a crude residue
  9. customIt was then purified with Combi Flash chromatography
  10. washeluting with 0 to 10% MeOH in DCM
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aee06529333f4a9dbfd95757eeda0445
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08067408B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes