1,2-Dichloroethane → Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate

HRID 564552Notes

Reaction equation

HRID 564552 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH3:23][O:24][C:25]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](O)=[O:31])=[O:26].C(Cl)CCl>C(Cl)Cl>[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:30]([C:29]3[CH:28]=[C:27]([CH:35]=[CH:34][CH:33]=3)[C:25]([O:24][CH3:23])=[O:26])=[O:31])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 57813262Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoateYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.02 g, 3 mmol) in DCM (30 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (541 mg, 3 mmol), EDC (633 mg, 3.3 mmol), and TEA (1.05 mL, 7.5 mmol). This mixture was stirred at room temperature for 18 h. The reaction mixture was washed with H2O (20 mL), dried over Na2SO4, filtered, concentrated and purified with CombiFlash to afford 0.7052 g (50%) of the title compound. LC-MS m/z 466 (M+H)+.

Workup

  1. washThe reaction mixture was washed with H2O (20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified with CombiFlash

Sources & evidence

ORD record
ord-b98863f600b943debde55c85141f2652
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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