Triethylamine → HCID 57813487, compound

HRID 564531Notes

Reaction equation

HRID 564531 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:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1)=[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:31]([C:30]3[CH:34]=[CH:35][C:27]([C:25]([O:24][CH3:23])=[O:26])=[CH:28][CH:29]=3)=[O:32])[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 15513Monomethyl terephthalateHCID 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 57813487HCID 57813487, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-amine (1.02 g, 3.0 mmol) in DCM (30 mL) was added 4-[(methyloxy)carbonyl]benzoic acid (0.541 g, 3.0 mmol), HBTU (1.37 g, 3.6 mmol), and Et3N (0.843 mL, 6.0 mmol) This mixture was stirred at room temperature for 23 h. It was diluted with DCM (30 mL), which was washed with H2O (30 mL) and dried over Na2SO4, filtered, concentrated and the concentrate purified by CombiFlash chromatograph to afford the title compound 1.40 g (quantitative). LC-MS m/z 466 (M+H)+.

Workup

  1. washwas washed with H2O (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe concentrate purified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-176fe9bd5a4840f18391033c3aab5956
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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