Diisopropylethylamine → HCID 67117259, compound

HRID 1193079Notes

Reaction equation

HRID 1193079 reaction equation
[C@@H:1]12[NH:8][CH2:7][C@@H:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]2.CCN(C(C)C)C(C)C.Cl[C:26]1[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=1>C(#N)C.O>[F:33][C:32]([F:35])([F:34])[C:30]1[CH:29]=[CH:28][N:27]=[C:26]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]3)[CH2:7]2)[N:31]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 16099092cis-3-Boc-3,8-diazabicyclo[4.2.0]octane

Product 1

HCID 67117259HCID 67117259, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To (1R,6S)-tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate (166 mg, 0.8 mmol) and DIPEA (404 μL, 2.3 mmol) in ACN (3.4 mL) was added 2-chloro-4-(trifluoromethyl)pyrimidine (110 μL, 0.9 mmol). The reaction mixture was heated at reflux for 2 h, cooled to rt, diluted with water and extracted with CH2Cl2 (2×). The combined organics were dried (Na2SO4) and concentrated to give 185 mg (66%) of the title compound as a clear oil which was used without further purification. MS (ESI) mass calcd. For C16H21F3N4O2, 358.40; m/z found 359.1 [M+H]+

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with CH2Cl2 (2×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8d8783a46b1491f876526f87b610920
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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