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 564434Notes

Reaction equation

HRID 564434 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(C(C)C)CC)(C)C>CN(C=O)C>[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

6

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 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine, previously described in WO2007036733A1, (250 mg, 0.83 mmol) in DMF (70 mL) was treated with 3-[(methyloxy)carbonyl]benzoic acid (149 mg, 0.83 mmol), PyBOP (473 mg, 0.91 mmol) and diisopropylethylamine (0.573 mL, 3.3 mmol) and the mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 h. The mixture was then concentrated to dryness and the residue treated with water (150 mL) and extracted with dichloromethane (2×100 mL). The combined organics were dried (hydrophobic frit) and concentrated to dryness to afford 383 mg of the title compound. LC-MS m/z 466 (M+H)+, 0.90 min (ret time).

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. additionthe residue treated with water (150 mL)
  3. extractionextracted with dichloromethane (2×100 mL)
  4. customThe combined organics were dried (hydrophobic frit)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8c4af3d626384845a0e5e3954f9ab0eb
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…