Diisopropylethylamine → 2-[2-[1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

HRID 451432Notes

Reaction equation

HRID 451432 reaction equation
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[N:4][N:3]=1.Cl[C:15]1[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[N:16]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:15]3[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=4)[N:16]=3)[CH2:11][CH2:12]2)=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 673446221-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamineHCID 866336402-[2-Chloro-6-(4-trifluoromethyl-phenyl)pyrimidine-4-yl]-propan-2-ol

Product 1

HCID 533535232-[2-[1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamine (36.5 mg, 0.2 mmol), 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol (69.1 mg, 0.22 mmol)) and N,N-diisopropylethylamine (52 L, 0.3 mmol) in dioxane (2 mL) was heated at 160° C. in a microwave oven for 5.5 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a white solid (29 mg, 31%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel with EtOAc/EtOH 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-0bef1254584347a796a48a588727f7e6
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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