Cesium carbonate → HCID 71283275, compound

HRID 1752451Notes

Reaction equation

HRID 1752451 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][C:11](=[O:31])[C@@H:12]([NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)[N:18]=[C:17]([C:28]([NH2:30])=[O:29])[CH:16]=1)[CH3:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:10][C:11](=[O:31])[CH:12]([NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:22][CH2:23][CH:24]([O:27][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[CH2:25][CH2:26]2)[N:18]=[C:17]([C:28]([NH2:30])=[O:29])[CH:16]=1)[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 145174-FluorobenzonitrileHCID 71283973HCID 71283973, compound

Product 1

HCID 71283275HCID 71283275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-fluorobenzonitrile (121 mg, 1 mmol), compound 37-7 (308 mg, 1 mmol), and Cs2CO3 (326 mg, 1 mmol) in DMF (2 mL) was heated at 160° C. in a microwave (Biotage initiator) for 20 minutes. The mixture was extracted with EtOAc (2×20 mL) and dried over MgSO4. After the removal of ethyl acetate via rotary evaporator the residue was subjected to flash chromatography using DCM/MeOH as the eluent to give S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-cyanophenoxy)piperidin-1-yl)pyrimidine-4-carboxamide (Cpd. No. 100) as a white solid (150 mg). 1H NMR (CD3OD) δ 7.55-7.65 (m, 2H), 7.12 (m, 2H), 6.40 (s, 1H), 4.80 (m, 1H), 4.30 (m, 1H), 3.95 (m, 2H), 3.68 (m, 2H), 1.98 (m, 2H), 1.75 (m, 2H), 1.40 (d, 3H). LC/MS: m/z=410 [M+H]+.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialdried over MgSO4
  3. customAfter the removal of ethyl acetate
  4. customvia rotary evaporator the residue

Sources & evidence

ORD record
ord-756157083a5647559aeed17d55088d2d
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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