Potassium Carbonate → HCID 56932421, compound

HRID 595013Notes

Reaction equation

HRID 595013 reaction equation
FC(F)(F)[C:3]([N:5](C)[CH2:6][C:7]1([CH2:11][N:12]2[CH:16]=[C:15]([NH:17][C:18]3[N:23]=[C:22]4[N:24]([CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[C:30]([N:34]6[CH2:39][CH2:38][O:37][CH2:36][CH2:35]6)[CH:29]=5)[N:25]=[CH:26][C:21]4=[CH:20][N:19]=3)[CH:14]=[N:13]2)[CH2:10][O:9][CH2:8]1)=O.C([O-])([O-])=O.[K+].[K+]>CO.O.CCOC(C)=O>[CH3:3][NH:5][CH2:6][C:7]1([CH2:11][N:12]2[CH:16]=[C:15]([NH:17][C:18]3[N:23]=[C:22]4[N:24]([CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[C:30]([N:34]6[CH2:39][CH2:38][O:37][CH2:36][CH2:35]6)[CH:29]=5)[N:25]=[CH:26][C:21]4=[CH:20][N:19]=3)[CH:14]=[N:13]2)[CH2:8][O:9][CH2:10]1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 86671742HCID 86671742, compound

Product 1

HCID 56932421HCID 56932421, compoundYield 10.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

2,2,2-trifluoro-N-methyl-N-((3-((4-((1-(3-morpholinobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methyl)acetamide (22 mg, 37.5 μmol) was dissolved in MeOH (1 mL) in a small vial. A solution of K2CO3 (26 mg, 187 μmol) in H2O (60 μL) was added to the solution, and the closed vial was heated at 55° C. for 1.5 h. The mixture was then diluted with EtOAc (7 mL) and washed with H2O (5 ml). The aqueous was extracted with a mixture of CHCl3/IPA=2:1 (3 mL×2). The organics were dried on Na2SO4, filtered and the solvent evaporated. The crude (22 mg) was purified by prep HPLC to give the title compound (2 mg). 1H NMR (d6-Acetone): δ 8.93 (s, 1H), 8.85 (s, 1H), 8.26 (s, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.71 (s, 1H), 7.17 (t, 1H), 7.05 (s, 1H), 6.85 (dd, J=8.0, 2.2 Hz, 1H), 6.80 (d, J=7.4 Hz, 1H), 5.52 (s, 2H), 4.59 (d, J=6.1 Hz, 2H), 4.50 (s, 2H), 4.34 (d, J=6.1 Hz, 2H), 3.72 (t, 4H), 3.06 (m, 4H), 2.52 (s, 2H), 2.38 (s, 3H); LC-MS method B, (ES+) 490.2, RT=5.08 min.

Workup

  1. washwashed with H2O (5 ml)
  2. extractionThe aqueous was extracted with a mixture of CHCl3/IPA=2:1 (3 mL×2)
  3. customThe organics were dried on Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe crude (22 mg) was purified by prep HPLC

Sources & evidence

ORD record
ord-f3989eca06c7419a86a960d07e7c550f
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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