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

HRID 564517Notes

Reaction equation

HRID 564517 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].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>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

6

Reactant 4

HCID 8471TriethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 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 62.3%

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]pyridine-4-amine (0.303 g, 1.0 mmol) in CH2Cl2 (10 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.198 g, 1.1 mmol), HBTU (0.569 g, 1.5 mmol), and Et3N (0.281 mL, 2.0 mmol). The mixture was stirred at room temperature for 22 h. The reaction was quenched with H2O (1 mL). The organic layer was separated, directly load onto silica gel cartridge and purified by CombiFlash chromatograph to afford the title compound 0.29 g (55%). LC-MS m/z 466 (M+H)+.

Workup

  1. customThe reaction was quenched with H2O (1 mL)
  2. customThe organic layer was separated
  3. customdirectly load onto silica gel cartridge and purified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-61f53ac38b524f5ba3001c8b31749cb7
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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