HCID 58456284, compound → HCID 58456402, compound

HRID 410547Notes

Reaction equation

HRID 410547 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([C:24]3[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH:25]=3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH:24]3[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 58456284HCID 58456284, compound

Product 1

HCID 58456402HCID 58456402, compoundYield 480%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-cyclohex-3-ene-1-carboxylate (0.15 g, 0.31 mmol) was added ethanol (2 mL) and argon was bubbled through the solution for 5 minutes. The flask was then purged/filled with argon three times. 10% Palladium on carbon (0.33 mg) was added to the flask and the flask was purged/filled with argon three times. A hydrogen balloon was added to the top of the flask and the reaction was purged/filled with argon three times. The reaction was stirred for 72 hours. Upon completion, the reaction was filtered carefully through celite and the celite pad was washed with methanol (70 mL). The filtrate was concentrated under reduced pressure and the solid was purified by silica gel chromatography to yield ethyl 4-[5-(3-methyl-5-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylate (0.73 g, 49% yield). MS ESI: [M+H]+ m/z 491.1. 1H NMR (500 MHz, CDCl3) δ 8.63 (d, J=5.3, 1H), 7.96-7.73 (m, 2H), 7.64 (s, 1H), 7.25 (s, 1H), 7.13-6.92 (m, 2H), 4.24-3.99 (m, 2H), 3.23-3.02 (m, 1H), 2.73-2.57 (m, 1H), 2.49 (s, 3H) 2.32-2.21 (m, 1H), 2.23-2.07 (m, 2H), 2.02-1.81 (m, 3H), 1.79-1.64 (m, 1H), 1.64-1.52 (m, 1H), 1.39-1.08 (m, 3H). rhSYK activity=++

Workup

  1. customwas bubbled through the solution for 5 minutes
  2. additionThe flask was then purged/filled with argon three times
  3. addition10% Palladium on carbon (0.33 mg) was added to the flask
  4. additionthe flask was purged/filled with argon three times
  5. additionA hydrogen balloon was added to the top of the flask
  6. additionthe reaction was purged/filled with argon three times
  7. filtrationUpon completion, the reaction was filtered carefully through celite
  8. washthe celite pad was washed with methanol (70 mL)
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e6f1d71463d413ea39c31da3852d17c
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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