Potassium Carbonate → HCID 71539516, compound

HRID 1466212Notes

Reaction equation

HRID 1466212 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.[C:48]([NH2:53])(=[O:52])[CH:49]([CH3:51])[CH3:50].N[C@@H]1CCCC[C@H]1N.C([O-])([O-])=O.[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]([NH:53][C:48](=[O:52])[CH:49]([CH3:51])[CH3:50])=[CH:10][N:9]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 68424IsobutyramideHCID 71539791HCID 71539791, compound

Product 1

HCID 71539516HCID 71539516, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °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 (150 mg, 0.207 mmol) and isobutyramide (0.018 g, 0.207 mmol) were dissolved in 1,4-dioxane (5 ml) in a sealed tube to which 1,2-transdiaminocyclohexane (0.007 g, 0.062 mmol), and CuI (0.007 g, 0.078 mmol) were added. The reaction mixture was de-gassed for 15 min with argon. K2CO3 (0.057 g, 0.414 mmol) was added to the reaction mixture and it was further degassed with argon for 15 min. The reaction mixture was then stirred at 80° C. for 3 days. Thereafter the reaction mixture was diluted with DCM-MeOH (3:1) mixture (10 ml), filtered through celite. The filtrate was concentrated under reduced pressure; purified by column chromatography using 60-120 silica gel and 25% EtOAc in petroleum ether as the eluent to obtain the title compound.

Workup

  1. additionwere added
  2. customThe reaction mixture was de-gassed for 15 min with argon
  3. customwas further degassed with argon for 15 min
  4. additionThereafter the reaction mixture was diluted with DCM-MeOH (3:1) mixture (10 ml)
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-a3b350e6395d4e4d90223dea9663a536
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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