Diisopropylethylamine → HCID 136623177, compound

HRID 2279164Notes

Reaction equation

HRID 2279164 reaction equation
[CH:1]1([C:4]2[C:12]3[C:11]([C:13](O)=[O:14])=[CH:10][C:9]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=4)=[N:8][C:7]=3[N:6]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[N:5]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:38]([O:42][C:43]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=[O:44])([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl.O>[C:38]([O:42][C:43]([N:45]1[CH2:50][CH2:49][N:48]([C:13]([C:11]2[C:12]3[C:4]([CH:1]4[CH2:3][CH2:2]4)=[N:5][N:6]([CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][O:24]4)[C:7]=3[N:8]=[C:9]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[CH:10]=2)=[O:14])[CH2:47][CH2:46]1)=[O:44])([CH3:41])([CH3:39])[CH3:40]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 136507827HCID 136507827, compound

Product 1

HCID 136623177HCID 136623177, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 0.80 g of 3-cyclopropyl-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 13 ml of DCM were added 1.4 ml of Hünig's base, 0.98 g of BEP and 0.47 g of tert-butyl-1-piperazine carboxylate. The reaction was stirred at r.t. for 4 h. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 0.79 g (68%) of the title compound.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

Sources & evidence

ORD record
ord-ff1dd015a3d34320b83c726033960393
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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