Potassium Carbonate → HCID 71539682, compound

HRID 1466217Notes

Reaction equation

HRID 1466217 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:17]=[C:18]2[C:33]([CH3:34])=[N:32][N:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:19]2=[N:20][C:21]=1[N:22]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[CH2:23][CH:24]1[CH2:26][CH2:25]1)[C:8]1[N:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[NH2:48][C@@H:49]1[CH2:54][CH2:53][CH2:52]C[C@H]1N.C([O-])([O-])=[O:57].[K+].[K+]>O1CCOCC1.[Cu]I>[CH:24]1([CH2:23][N:22]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:21]2[N:20]=[C:19]3[N:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[N:32]=[C:33]([CH3:34])[C:18]3=[CH:17][C:16]=2[CH2:15][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:47])([F:46])[F:1])[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=2)[C:8]2[N:13]=[CH:12][C:11]([N:48]3[CH2:52][CH2:53][CH2:54][C:49]3=[O:57])=[CH:10][N:9]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 71539791HCID 71539791, compound

Product 1

HCID 71539682HCID 71539682, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-(((3,5-Bis(trifluoromethyl)benzyl)(5-bromopyrimidin-2-yl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine (0.2 g, 0.293 mmol), obtained in step (vi) of Example 1,2-pyrrolidinone (0.024 g, 0.293 mmol), CuI (0.005 mg, 0.029 mmol), trans-1,2-diaminocyclohexane (0.007 g, 0.064 mmol) were taken in a sealed tube in 1,4-dioxane (5 mL), which was degassed with argon for 15 min. K2CO3 (0.08 g, 0.586 mmol) was added to it. The reaction mixture was stirred at 100° C. for 28 h. Thereafter the reaction mixture was filtered through celite, extracted with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography using EtOAc-petroleum ether as eluent to obtain the title compound.

Workup

  1. customwhich was degassed with argon for 15 min
  2. filtrationThereafter the reaction mixture was filtered through celite
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-38d001ee03b6433db5aa912ec43084a2
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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