Ethyl Acetate → 3-{[[(3-Bromo-4-fluorophenyl)methyl](methyl)amino]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide

HRID 564520Notes

Reaction equation

HRID 564520 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[C:6]([NH:8][CH2:9][C:10]1[C:11]([NH:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[C:12]2[CH:20]=[N:19][N:18]([CH2:21][CH3:22])[C:13]2=[N:14][C:15]=1[CH2:16][CH3:17])=[O:7].[Br:33][C:34]1[CH:35]=[C:36]([CH2:41][NH:42][CH3:43])[CH:37]=[CH:38][C:39]=1[F:40].CCOC(C)=O>CN(C=O)C>[Br:33][C:34]1[CH:35]=[C:36]([CH2:41][N:42]([CH2:2][C:3]2[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=2)[C:6]([NH:8][CH2:9][C:10]2[C:11]([NH:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[C:12]3[CH:20]=[N:19][N:18]([CH2:21][CH3:22])[C:13]3=[N:14][C:15]=2[CH2:16][CH3:17])=[O:7])[CH3:43])[CH:37]=[CH:38][C:39]=1[F:40]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 16781426[(3-Bromo-4-fluorophenyl)methyl](methyl)amineHCID 578134963-(Chloromethyl)-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide

Product 1

HCID 578133763-{[[(3-Bromo-4-fluorophenyl)methyl](methyl)amino]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(chloromethyl)-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide (0.284 g, 0.623 mmol) in DMF (2.5 mL) was added [(3-bromo-4-fluorophenyl)methyl]methylamine (0.436 g, 2.0 mmol). This mixture was stirred at room temperature for 66 h. Then EtOAc (50 mL) was added and that solution washed with H2O (7.5+2×5 mL), brine (5 mL), dried over Na2SO4. The dried organic solution was filtered, concentrated and purified by CombiFlash chromatograph to afford the title compound 0.371 g (93%). LC-MS m/z 637 (M+H)+.

Workup

  1. washwashed with H2O (7.5+2×5 mL), brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationThe dried organic solution was filtered
  4. concentrationconcentrated
  5. custompurified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-383be64944f64ab19610e296268d022e
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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