Ethyl Acetate → HCID 86659172, compound

HRID 2367236Notes

Reaction equation

HRID 2367236 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](S(C)(=O)=O)[N:5]=[C:4]([N:12]2[C@H:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH2:15][C@H:14]([C:22]([NH:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[CH2:13]2)[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:40][O:41][C:42]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=1[CH2:50][NH2:51].CCOC(C)=O>O1CCOCC1>[CH3:40][O:41][C:42]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:43]=1[CH2:50][NH:51][C:6]1[N:5]=[C:4]([N:12]2[C@H:17]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH2:15][C@H:14]([C:22]([NH:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[CH2:13]2)[CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 5972502,4-DimethoxybenzylamineHCID 86659171HCID 86659171, compound

Product 1

HCID 86659172HCID 86659172, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To cis-1-[6-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (300 mg, 0.640 mmol) in 1,4-dioxane (8 mL) was added Hunig's base (0.22 mL, 1.28 mmol) followed by {[2,4-bis(methyloxy)phenyl]methyl}amine (0.19 mL, 1.28 mmol), and the reaction mixture was stirred overnight at 60° C. into a sealed tube. This reaction mixture was combined with another similar reaction mixture (˜⅓ the scale) before work up. The combined reaction mixtures were poured onto water and EtOAc. The layers were separated, and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% Hexanes to 50% EtOAc in Hexanes) afforded the title compound (322 mg) as a white foam. LC-MS (ES) m/z=556 [M+H]+.

Workup

  1. customThe combined reaction mixtures
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06eadf78513249fbaed112e58817d610
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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