Sodium → HCID 58504597, compound

HRID 2367613Notes

Reaction equation

HRID 2367613 reaction equation
[CH3:1][O-:2].[Na+].[Na].[F:5][C:6]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][C@H:21]3[C:25]([F:28])([F:27])[F:26])[N:17]=[C:16]([NH:29][CH3:30])[N:15]=2)[CH:11]=[C:10](F)[C:7]=1[C:8]#[N:9]>CO>[F:5][C:6]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][C@H:21]3[C:25]([F:28])([F:27])[F:26])[N:17]=[C:16]([NH:29][CH3:30])[N:15]=2)[CH:11]=[C:10]([O:2][CH3:1])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 58504530HCID 58504530, compound

Product 1

HCID 58504597HCID 58504597, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide was made from 65 mg of sodium dissolved in 2.8 mL of CH3OH. From that solution 0.4 mL was added to a predissolved solution of 2,6-difluoro-4-{2-(methylamino)-6-[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile (127 mg, 0.331 mmol) in CH3OH (3 mL). The reaction was stirred at room temperature overnight. The reaction was concentrated, then diluted with water (15 mL) and extracted with EtOAc (3×15 mL). The organic was combined, dried over MgSO4, filtered and concentrated to afford the crude title compound (131 mg). LC-MS (ES) m/z=396 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water (15 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b31744c4e15e49869029d939d3b2471c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…