Sodium Bicarbonate → HCID 58504609, compound

HRID 2367421Notes

Reaction equation

HRID 2367421 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][C@@H:21]([NH2:23])[CH2:20][CH2:19][C@H:18]2[CH3:24])[N:3]=1.[C:25]([O-:28])(O)=[O:26].[Na+]>C1COCC1.O>[C:8]1([CH2:6][O:28][C:25](=[O:26])[NH:23][C@H:21]2[CH2:20][CH2:19][C@@H:18]([CH3:24])[N:17]([C:4]3[CH:5]=[C:6]([C:8]4[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=4)[N:7]=[C:2]([NH2:1])[N:3]=3)[CH2:22]2)[CH:15]=[CH:14][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58504797HCID 58504797, compound

Product 1

HCID 58504609HCID 58504609, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{2-amino-6-[(2R,5S)-5-amino-2-methyl-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (170 mg, 0.426 mmol) in THF (4 mL) was added saturated aqueous NaHCO3 (2 mL) followed by phenylmethyl chloridocarbonate (0.07 mL, 0.47 mmol), and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with 3 mL of water and then extracted with EtOAc (3×30 mL). The organic was then washed with brine, dried over MgSO4, filtered and concentrated. The resulting yellow oil was purified on a Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 30 minutes to afford the title compound (57 mg) as a yellow oil. LC-MS (ES) m/z=327 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe organic was then washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting yellow oil was purified on a Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 30 minutes

Sources & evidence

ORD record
ord-de0ef1dcfc134fa6bc0359db55aeb1b8
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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