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

HRID 564484Notes

Reaction equation

HRID 564484 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].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.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

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 2724699PyBOPHCID 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]benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 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 (0.6 g, 2 mmol) stirring at room temperature under argon in DMF (150 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.356 g, 2 mmol), followed by PyBOP (1.14 g, 2.2 mmol), and N,N-diisopropylethylamine (1.38 mL, 8 mmol). The mixture was stirred at room temperature for 17 h. The solvent was pumped off, and the residue taken up in CH2Cl2 (300 mL), and washed with water (300 mL). The organic phase dried over anhydrous Na2SO4, filtered and concentrated. This was then CombiFlashed on a 40 gram silica column eluted with 20-100% EtOAc to afford the title compound. LC-MS m/z 465.8 (M+H)+, 1.49 min (ret time).

Workup

  1. washwashed with water (300 mL)
  2. dry with materialThe organic phase dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 20-100% EtOAc

Sources & evidence

ORD record
ord-d10b6bf8650b416e91eaba551381b0b2
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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