Sodium Bicarbonate → HCID 58504428, compound

HRID 2367621Notes

Reaction equation

HRID 2367621 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][CH2:21][CH2:20][C@@H:19]([NH2:23])[CH2:18]2)[N:3]=1.[C:24]([O-:27])(O)=[O:25].[Na+]>C1COCC1.O>[C:8]1([CH2:6][O:27][C:24](=[O:25])[NH:23][C@@H:19]2[CH2:20][CH2:21][CH2:22][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)[CH2:18]2)[CH:15]=[CH:14][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58504655HCID 58504655, compound

Product 1

HCID 58504428HCID 58504428, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-{2-amino-6-[(3R)-3-amino-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (125 mg, 0.324 mmol) in THF (4 mL) and saturated NaHCO3 (2 mL) was added phenylmethyl chloridocarbonate (0.055 mL, 0.389 mmol), and the resulting mixture was stirred at room temperature overnight. The reaction was diluted with water (10 mL), then extracted with EtOAc (3×10 mL). The organic was combined, washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated to afford the crude title compound (155 mg) as a yellow oil. LC-MS (ES) m/z=447 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5c2d52f0c494ee18011bd2558b25c16
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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