Methylamine → HCID 86659173, compound

HRID 2367240Notes

Reaction equation

HRID 2367240 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.C[CH2:32][N:33](C(C)C)C(C)C.CN.C1COCC1>O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:33][CH3:32])[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

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 86659171HCID 86659171, compound

Product 1

HCID 86659173HCID 86659173, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To cis-1-[6-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (390 mg, 0.832 mmol) in 1,4-dioxane (8 mL) was added Hunig's base (0.29 mL, 1.66 mmol) followed by 2M methylamine in THF (1 mL, 2 mmol), and the reaction mixture was stirred overnight at 60° C. into a sealed tube. The mixture was poured onto water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% Hexanes to 50% EtOAc in Hexanes) afforded the title compound (204 mg) as a white foam. LC-MS (ES) m/z=420, 422 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0309e8e79e604b00b6ed10aae2bd5474
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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