Diisopropylethylamine → 3-(((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)amino)-4-ethoxycyclobut-3-ene-1,2-dione

HRID 2098372Notes

Reaction equation

HRID 2098372 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[C:10]([CH2:11][CH3:12])=[N:9][C:8]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:7]=2[C:6]=1[NH:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)C(C)C)(C)C.[CH2:34]([O:36][C:37]1[C:38](=O)[C:39](=[O:44])[C:40]=1[O:41]CC)[CH3:35]>C(O)C>[CH2:16]([N:13]1[C:8]2=[N:9][C:10]([CH2:11][CH3:12])=[C:5]([CH2:4][NH:3][C:38]3[C:39](=[O:44])[C:40](=[O:41])[C:37]=3[O:36][CH2:34][CH3:35])[C:6]([NH:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[C:7]2[CH:15]=[N:14]1)[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123228Diethyl squarateHCID 669893455-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine dihydrochloride

Product 1

HCID 585052993-(((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)amino)-4-ethoxycyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine dihydrochloride (0.60 g, 1.6 mmol) in ethanol (8 mL) was treated with N,N-diisopropylethylamine (DIEA, 0.57 mL, 3.3 mmol), giving a clear, homogeneous mixture, which was then cooled in an ice-water bath. 3,4-Diethoxycyclobut-3-ene-1,2-dione (TCI America, 0.41 g, 0.36 mmol) was then added dropwise via syringe. Following completion of the addition, the mixture was allowed to regain room temperature and stir overnight. The precipitated solid was collected by Büchner filtration, washed with ethanol, and dried under house vacuum to provide the title compound as a white solid. ES/MS calcd. for C22H30N5O4+ 428.2, found m/z=428.3 (M+H)+.

Workup

  1. customgiving a clear, homogeneous mixture, which
  2. temperaturewas then cooled in an ice-water bath
  3. additioncompletion of the addition
  4. customto regain room temperature
  5. filtrationThe precipitated solid was collected by Büchner filtration
  6. washwashed with ethanol
  7. customdried under house vacuum

Sources & evidence

ORD record
ord-207ebcae5aed4eb78f9be78405a88465
Source dataset
uspto-grants-2013_05
Patent number
US08450490B2

Reaction notes

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