Triethylamine → HCID 67113434, compound

HRID 2088904Notes

Reaction equation

HRID 2088904 reaction equation
Cl[C:2]1[C:3]2[C@H:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:14][C:15]([F:35])([F:34])[C:16]1[N:17]=[C:18]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[N:19]([CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:20]=1.C(N(CC)CC)C>CN1CCCC1=O>[CH3:12][C@H:11]1[C:3]2[C:2]([N:31]3[CH2:30][CH2:29][CH:28]([C:18]4[N:19]([CH2:21][CH2:22][N:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[CH:20]=[C:16]([C:15]([F:34])([F:35])[F:14])[N:17]=4)[CH2:33][CH2:32]3)=[N:7][CH:6]=[N:5][C:4]=2[NH:8][C:9](=[O:13])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67113455HCID 67113455, compoundHCID 86666575(R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 67113434HCID 67113434, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

Add (R)-4-chloro-5-methyl-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (28.30 g, 143.20 mmol), 4-(4-trifluoromethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine (49.83 g, 1.10 eq) and triethylamine (43.47 g, 3.0 eq) in N-methylpyrrolidinone (86 mL). Heat the reaction mixture to 130° C. Cool the reaction mixture to room temperature after 2 hours. Pour the reaction mixture over ice/water (500 mL) with stirring. Extract with ethyl acetate (4×200 mL). Wash the organics with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate and concentrate in vacuo. Suspend the solid in hexanes and stir for 30 minutes. Filter and dry under vacuum. Add 75% methyl tert-butyl ether in hexanes (800 mL) and heat to reflux. Cool the mixture to room temperature. Filter, wash with 75% methyl tert-butyl ether in hexanes (200 mL), and dry under vacuum at 40° C. to give the title compound (48.00 g, 70%). MS (ES) m/z=478 [M]+.

Workup

  1. temperatureCool the reaction mixture to room temperature after 2 hours
  2. extractionExtract with ethyl acetate (4×200 mL)
  3. washWash the organics with saturated aqueous sodium chloride solution
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate in vacuo
  6. stirringstir for 30 minutes
  7. filtrationFilter
  8. customdry under vacuum
  9. additionAdd 75% methyl tert-butyl ether in hexanes (800 mL)
  10. temperatureheat to reflux
  11. temperatureCool the mixture to room temperature
  12. filtrationFilter
  13. washwash with 75% methyl tert-butyl ether in hexanes (200 mL)
  14. customdry under vacuum at 40° C.

Sources & evidence

ORD record
ord-1cb6f4c501f345a69c01504da928ee39
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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