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

HRID 564561Notes

Reaction equation

HRID 564561 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].C(OC(Cl)=O)C.[NH2:20][CH2:21][C:22]1[C:27]([CH2:28][CH3:29])=[N:26][C:25]2[N:30]([CH2:33][CH3:34])[N:31]=[CH:32][C:24]=2[C:23]=1[NH:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(Cl)Cl>[CH2:33]([N:30]1[C:25]2=[N:26][C:27]([CH2:28][CH3:29])=[C:22]([CH2:21][NH:20][C:8]([C:7]3[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=3)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[C:23]([NH:35][CH:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[C:24]2[CH:32]=[N:31]1)[CH3:34]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 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 107.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-(methoxycarbonyl)benzoic acid (1.261 g, 7.00 mmol) in DCM (35 mL) was added TEA (2.439 mL, 17.50 mmol), EtOCOCl (0.739 mL, 7.70 mmol) at 0° C. after which 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (2.379 g, 7.00 mmol) was added. This mixture was then stirred for 1 h at room temperature. The reaction mixture was diluted with DCM (35 mL) then washed with HOAc (2×20 mL, 10%), NaHCO3 (20 mL, 10%), and water (20 mL), concentrated, The residue washed with EtOAc/Hexane (10 mL, 1:1) to afford the title compound (3.5138 g, 94.2%). LC-MS m/z 466 (M+H)+.

Workup

  1. additionwas added
  2. washthen washed with HOAc (2×20 mL, 10%), NaHCO3 (20 mL, 10%), and water (20 mL)
  3. concentrationconcentrated
  4. washThe residue washed with EtOAc/Hexane (10 mL, 1:1)

Sources & evidence

ORD record
ord-51da0c0829ec46c8bb01157203bbf6e5
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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