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

HRID 657299
Notes
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Reaction equation

HRID 657299 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12](=[O:38])[CH2:13][C:14]([NH:16][CH2:17][C:18]2[C:19]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:20]3[CH:28]=[N:27][N:26]([CH2:29][CH3:30])[C:21]3=[N:22][C:23]=2[CH2:24][CH3:25])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:39]([C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1)=[O:40].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>CCOC(C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:29]([N:26]1[C:21]2=[N:22][C:23]([CH2:24][CH3:25])=[C:18]([CH2:17][NH:16][C:14](=[O:15])[CH2:13][C:12]([NH:11][CH2:10][C:4]3[CH:3]=[C:2]([C:45]4[CH:44]=[CH:43][CH:42]=[C:41]([CH:39]=[O:40])[CH:46]=4)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=3)=[O:38])[C:19]([NH:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:20]2[CH:28]=[N:27]1)[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343563-Formylphenylboronic acidHCID 57819863N-{[3-bromo-4-(methyloxy)phenyl]methyl}-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide

Product 1

HCID 57819930
N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[3'-formyl-6-(methyloxy)-3-biphenylyl]methyl}propanediamide
Yield 91%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-{[3-bromo-4-(methyloxy)phenyl]methyl}-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (0.800 g, 1.362 mmol), (3-formylphenyl)boronic acid (0.225 g, 1.5 mmol), tetrakis (triphenylphosphine) palladium (0) (0.058 g, 0.05 mmol), sodium carbonate (0.371 g, 3.5 mmol), and 1,4-dioxane (12 ml) and water (4 ml), with stirring under N2, was microwaved at 140° C. for 30 minutes. The reaction mixture was diluted with EtOAc and water and the organic layer taken off. It was washed with saturated NaCl, dried over Na2SO4, and evaporated resulting in a viscous taffy. The viscous taffy was purified on a Chromatotron Plate Silica Gel (1000μ) eluting with CH2Cl2— MeOH (97:3) to afford N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[3′-formyl-6-(methyloxy)-3-biphenylyl]methyl}propanediamide (526 mg, 91%) as a viscous, nearly colorless, taffy. LC-MS m/z 613.4 (M+H)+, 0.81 min (ret time).

Workup

  1. customwas microwaved at 140° C. for 30 minutes
  2. washIt was washed with saturated NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customresulting in a viscous taffy
  6. customThe viscous taffy was purified on a Chromatotron Plate Silica Gel (1000μ)
  7. washeluting with CH2Cl2— MeOH (97:3)

Sources & evidence

ORD record
ord-39fcfce1beaa4565853fe636e3653ac4
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes